WO2018114073A1 - Riechstoffmischung - Google Patents
Riechstoffmischung Download PDFInfo
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- WO2018114073A1 WO2018114073A1 PCT/EP2017/074461 EP2017074461W WO2018114073A1 WO 2018114073 A1 WO2018114073 A1 WO 2018114073A1 EP 2017074461 W EP2017074461 W EP 2017074461W WO 2018114073 A1 WO2018114073 A1 WO 2018114073A1
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- WIPO (PCT)
- Prior art keywords
- formula
- acid
- methyl
- compounds
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- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 181
- 239000003205 fragrance Substances 0.000 title claims abstract description 92
- 150000001875 compounds Chemical class 0.000 claims abstract description 109
- 239000003921 oil Substances 0.000 claims abstract description 75
- 239000002304 perfume Substances 0.000 claims abstract description 75
- 239000003599 detergent Substances 0.000 claims abstract description 72
- 150000002148 esters Chemical class 0.000 claims abstract description 64
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 55
- 239000002537 cosmetic Substances 0.000 claims abstract description 25
- 239000012459 cleaning agent Substances 0.000 claims abstract description 21
- PEOYDDSUGYIYGS-VMPITWQZSA-N diethyl 2-[(e)-but-2-en-2-yl]propanedioate Chemical compound CCOC(=O)C(\C(C)=C\C)C(=O)OCC PEOYDDSUGYIYGS-VMPITWQZSA-N 0.000 claims abstract description 9
- PEOYDDSUGYIYGS-YVMONPNESA-N diethyl 2-[(z)-but-2-en-2-yl]propanedioate Chemical compound CCOC(=O)C(\C(C)=C/C)C(=O)OCC PEOYDDSUGYIYGS-YVMONPNESA-N 0.000 claims abstract 2
- -1 Aliphatic alcohols Chemical class 0.000 claims description 219
- 125000004432 carbon atom Chemical group C* 0.000 claims description 62
- 239000000126 substance Substances 0.000 claims description 57
- 239000002253 acid Substances 0.000 claims description 41
- 239000006210 lotion Substances 0.000 claims description 40
- 239000007788 liquid Substances 0.000 claims description 37
- 238000002360 preparation method Methods 0.000 claims description 36
- 239000002904 solvent Substances 0.000 claims description 34
- 239000006071 cream Substances 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 29
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- 150000001298 alcohols Chemical class 0.000 claims description 24
- 150000002170 ethers Chemical class 0.000 claims description 22
- 210000004209 hair Anatomy 0.000 claims description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
- 239000002781 deodorant agent Substances 0.000 claims description 20
- 230000008569 process Effects 0.000 claims description 20
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
- 238000004519 manufacturing process Methods 0.000 claims description 18
- 239000000344 soap Substances 0.000 claims description 18
- HNEGQIOMVPPMNR-NSCUHMNNSA-N mesaconic acid Chemical compound OC(=O)C(/C)=C/C(O)=O HNEGQIOMVPPMNR-NSCUHMNNSA-N 0.000 claims description 17
- 239000000499 gel Substances 0.000 claims description 16
- HNEGQIOMVPPMNR-UHFFFAOYSA-N methylfumaric acid Natural products OC(=O)C(C)=CC(O)=O HNEGQIOMVPPMNR-UHFFFAOYSA-N 0.000 claims description 16
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 11
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- 125000003118 aryl group Chemical group 0.000 claims description 9
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- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 claims description 8
- 125000004122 cyclic group Chemical group 0.000 claims description 8
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- 229910052740 iodine Inorganic materials 0.000 claims description 8
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- 125000001931 aliphatic group Chemical group 0.000 claims description 7
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
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- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims description 3
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- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
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- 235000002639 sodium chloride Nutrition 0.000 description 51
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- WCTNXGFHEZQHDR-UHFFFAOYSA-N valencene Natural products C1CC(C)(C)C2(C)CC(C(=C)C)CCC2=C1 WCTNXGFHEZQHDR-UHFFFAOYSA-N 0.000 description 1
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- 229940045997 vitamin a Drugs 0.000 description 1
- 239000001529 viverra civetta schreber and viverra zibeth a schreber absolute Substances 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
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- QRPLZGZHJABGRS-UHFFFAOYSA-N xi-5-Dodecanolide Chemical compound CCCCCCCC1CCCC(=O)O1 QRPLZGZHJABGRS-UHFFFAOYSA-N 0.000 description 1
- WGPCZPLRVAWXPW-UHFFFAOYSA-N xi-Dihydro-5-octyl-2(3H)-furanone Chemical compound CCCCCCCCC1CCC(=O)O1 WGPCZPLRVAWXPW-UHFFFAOYSA-N 0.000 description 1
- PHXATPHONSXBIL-UHFFFAOYSA-N xi-gamma-Undecalactone Chemical compound CCCCCCCC1CCC(=O)O1 PHXATPHONSXBIL-UHFFFAOYSA-N 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
- 229960003487 xylose Drugs 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
- 229910001845 yogo sapphire Inorganic materials 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 229940071566 zinc glycinate Drugs 0.000 description 1
- 229940043810 zinc pyrithione Drugs 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
- 239000011686 zinc sulphate Substances 0.000 description 1
- 235000009529 zinc sulphate Nutrition 0.000 description 1
- PICXIOQBANWBIZ-UHFFFAOYSA-N zinc;1-oxidopyridine-2-thione Chemical compound [Zn+2].[O-]N1C=CC=CC1=S.[O-]N1C=CC=CC1=S PICXIOQBANWBIZ-UHFFFAOYSA-N 0.000 description 1
- UOXSXMSTSYWNMH-UHFFFAOYSA-L zinc;2-aminoacetate Chemical compound [Zn+2].NCC([O-])=O.NCC([O-])=O UOXSXMSTSYWNMH-UHFFFAOYSA-L 0.000 description 1
- UZFLPKAIBPNNCA-FPLPWBNLSA-N α-ionone Chemical compound CC(=O)\C=C/C1C(C)=CCCC1(C)C UZFLPKAIBPNNCA-FPLPWBNLSA-N 0.000 description 1
- PFSTYGCNVAVZBK-KVDYQJCMSA-N α-sinensal Chemical compound O=CC(\C)=C/CCC(/C)=C/C\C=C(\C)C=C PFSTYGCNVAVZBK-KVDYQJCMSA-N 0.000 description 1
- YHQGMYUVUMAZJR-UHFFFAOYSA-N α-terpinene Chemical compound CC(C)C1=CC=C(C)CC1 YHQGMYUVUMAZJR-UHFFFAOYSA-N 0.000 description 1
- OENHQHLEOONYIE-JLTXGRSLSA-N β-Carotene Chemical compound CC=1CCCC(C)(C)C=1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C OENHQHLEOONYIE-JLTXGRSLSA-N 0.000 description 1
- 229930007850 β-damascenone Natural products 0.000 description 1
- NOPLRNXKHZRXHT-PVMFERMNSA-N β-sinensal Chemical compound O=CC(\C)=C/CCC(/C)=C/CCC(=C)C=C NOPLRNXKHZRXHT-PVMFERMNSA-N 0.000 description 1
- QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 0.000 description 1
Classifications
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- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/202—Aliphatic compounds
- A23L27/2024—Aliphatic compounds having oxygen as the only hetero atom
- A23L27/2028—Carboxy compounds
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0007—Aliphatic compounds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
- C07C69/593—Dicarboxylic acid esters having only one carbon-to-carbon double bond
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/37—Esters of carboxylic acids
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/54—Preparation of carboxylic acid anhydrides
- C07C51/56—Preparation of carboxylic acid anhydrides from organic acids, their salts, their esters or their halides, e.g. by carboxylation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/12—Preparation of carboxylic acid esters from asymmetrical anhydrides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/36—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/60—Two oxygen atoms, e.g. succinic anhydride
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0007—Aliphatic compounds
- C11B9/0015—Aliphatic compounds containing oxygen as the only heteroatom
- C11B9/0019—Aliphatic compounds containing oxygen as the only heteroatom carbocylic acids; Salts or esters thereof
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/50—Perfumes
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q13/00—Formulations or additives for perfume preparations
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- A61Q15/00—Anti-perspirants or body deodorants
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/02—Preparations for cleaning the hair
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/10—Preparations for permanently dyeing the hair
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/12—Preparations containing hair conditioners
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
- C11D7/22—Organic compounds
- C11D7/26—Organic compounds containing oxygen
- C11D7/266—Esters or carbonates
Definitions
- the invention is in the field of fragrances and relates to fruity, pear-like fragrance mixtures, to compositions containing the particular fragrances or perfume mixtures, to processes for producing pear-like perfumes, to a perfuming process and to the use of special fragrances for production a pear-like fragrance.
- fragrances that are not only distinguished by new original fragrances, but also have additional positive secondary properties beyond their olfactory properties, such as. B. higher stability and yield under certain conditions of use, a better adhesion, a greater radiation power, a lower threshold or even better dermatological and toxicological results, such. a good biodegradability.
- fragrances which, at a lower dosage, make the same or higher fragrance contribution than comparable substances and thus lead to a lower input into the environment (low-volume-high impact). Or that can be made significantly cheaper at a same fragrance contribution.
- perfumes with complex odor properties such as e.g. fruity pear-like.
- acetic acid amyl ester otherwise known for its pear-like flavor, does not meet these conditions.
- the object of the present has therefore been to provide fragrances and perfume compositions with pear-like flavor available based on renewable raw materials, preferably waste materials, which overcome the disadvantages of the prior art, ie in particular at low dosages a high fragrance contribution afford, simple and stable in a variety of perfume and final product formulations can be incorporated and thereby be produced with low technical complexity and at low cost.
- a first aspect of the invention relates to a fragrance mixture containing a sensory effective amount of one, two or all three compounds from the group formed by: formula (i), formula (ii), and formula (iii ):
- each R1 represents a linear, branched or cydic alkyl radical having 1 to 10 carbon atoms, preferably a methyl or ethyl group, an araliphatic or aromatic radical
- each R2 is a linear, branched or cyclic alkyl radical having 1 to 10 carbon atoms, preferably a methyl or ethyl group, an araliphatic or aromatic radical.
- the compounds of the formula (i) are suitable as pear-like fragrance and in the process fully meet the complex requirement profile described above.
- the substances of the formula (ii) and of the formula (iii) are involved in the preparation and also have a weakened pear-like flavor. It is particularly noteworthy that these are substances that are obtained from renewable raw materials, especially from waste of the sugar industry. It was also surprising that these substances can be permanently incorporated in a stable manner in a large number of different formulations and, in particular, exceed the standard of the ethylenecadienoates.
- R 1 and R 2 are each an identical or different linear, branched or cyclic alkyl radical having 1 to 8 or 1 to 6 carbon atoms, preferably a methyl or ethyl group.
- the linear radicals are in this case emphasized valuable, especially for alkyl radicals having 1 to 4 carbon atoms.
- branched alkyl radicals having this carbon atom number are preferred.
- the group of preferred linear alkyl radicals for R1 and R2 of 1 to 10 carbon atoms in the compounds of formula (i), formula (ii) and / or formula (iii) is formed from the following radical radicals: methyl, ethyl , n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl and n-decyl.
- Preferred linear alkyl radicals are methyl, ethyl, but also suitable are n-propyl, n-butyl, n-pentyl and n-hexyl.
- Particularly preferred linear alkyl radicals are methyl, ethyl, n-propyl and n-butyl.
- the group of branched alkyl radicals for R 1 and R 2 having 1 to 10 carbon atoms in the compounds of the formula (i), of the formula (ii) and / or of the formula (iii) is formed from: isopropyl, isobutyl, sec. Butyl, tert-butyl, isopentyl, tert-pentyl, iso-hexyl, tert-hexyl, iso-heptyl, iso-octyl, tert-octyl, iso-nonyl, tert-nonyl, tert-decyl and isodecyl.
- Preferred branched alkyl radicals are isopropyl, isobutyl, sec-butyl and tert-butyl. Particularly preferred branched alkyl radicals are isopropyl and isobutyl.
- the group of the cyclic alkyl radicals for R 1 and R 2 having 1 to 10 carbon atoms in the compounds of the formula (i), the formula (ii) and / or the formula (iii) is formed from: cyclopropane, cyclobutane, cyclopentane, cyclohexane , Cycloheptane and cyclooctane.
- Preferred cyclic alkyl radicals are cyclopentane and cyclohexane.
- the group of araliphatic radicals R 1 and R 2 in the compounds of the formula (i), of the formula (ii) and / or of the formula (iii) is to be understood as meaning an alkyl radical in which one or more hydrogen atoms are represented by an aromatic radical are replaced.
- the group of araliphatic radicals in the compounds of the formula (i), of the formula (ii) and / or of the formula (iii) is formed from: toluene, 2-methylfuran, 3 Methyl furan, picolines, cresols, xylenes, 1-methylnaphthalene, 2-methylnaphthalene and ethylbenzene.
- Preferred araliphatic radicals are toluene and ethylbenzene.
- the group of aromatic radicals for R 1 and R 2 in the compounds of the formula (i), of the formula (ii) and / or of the formula (iii) is formed from: pyrimidines, furan, thiran, benzene, naphthalene, phenol, Pyridine and benzodiazepines.
- Preferred aromatic radicals are furan and benzene.
- a sensory effective amount means a proportion of the substances of the formula (i), of the formula (ii) and / or of the formula (iii) in the mixture which is sufficient to produce a fruity, pear-like odor impression .
- This fruity pear-like olfactory impression will in principle be evoked when at least 0.001% by weight of the fragrance mixture is present through one, two or all three compounds of formula (i), formula (ii) and formula (iii).
- the radical R 1 and / or R 2 in the compounds of the formula (i), of the formula (ii) and of the formula (iii) in the above-described fragrance mixture are each independently of one another a C 1 to C 4 Rest, ie in particular a methyl, ethyl, propyl, and butyl radical. These compounds are particularly easy to manufacture and show the most impressive odor profiles.
- the radical R 1 in the compounds of the formula (i), of the formula (ii) and of the formula (iii) in the above-described fragrance mixture is in each case independently of one another methyl, ethyl, Propyl, and / or butyl radical and the radical R2 in the compounds of formula (i), the formula (ii) and the formula (iii) in the above-described fragrance mixture each independently a methyl radical or ethyl radical.
- the radical R 2 in the compounds of the formula (i), of the formula (ii) and of the formula (iii) in the above-described fragrance mixture is in each case independently of one another methyl, ethyl, Propyl and butyl radical and the radical R1 in the compounds of the formula (i), of the formula (ii) and the formula (iii) in the above-described fragrance mixture are each independently a methyl radical or ethyl radical.
- radicals R 1 and R 2 in the compounds of the formula (i), of the formula (ii) and of the formula (iii) in the above-described fragrance mixture are each the same radicals. This simplifies the production.
- the radicals R 1 and R 2 in the compounds of the formula (i), of the formula (ii) and of the formula (iii) in the described fragrance mixture are each independently selected from the group formed is derived from: linear or branched methyl, ethyl, propyl, and butyl alkyl radicals. Especially the linear alkyl radicals and shorter branched alkyl radicals are suitable to fit into the odor binding pockets.
- radicals R 1 and R 2 in the compounds of the formula (i), of the formula (ii) and of the formula (iii) in the above-described fragrance mixture are each independently of one another methyl, ethyl, Propyl and butyl radicals.
- radicals R 1 and R 2 in the compounds of the formula (i), of the formula (ii) and of the formula (iii) in the above-described fragrance mixture are each independently methyl, and propyl residues.
- the invention relates to a fragrance mixture containing a sensory effective amount of one, two or all three compounds from the group formed by:
- Fragrances In the fragrances of the present invention, the substance ('Ej-2-methyl-but-2-endicarboxylic acid diethyl ester of the formula (I)
- the two compounds of formula (ii) and formula (iii) are citraconic acid diethyl ester and diethyl itaconate, which are generally obtained together with the diethyl mesaconate as isomer mixture in the preparation.
- Particularly preferred for compound (ii) is the () -2-methylbutano 2-endicarboxylic acid diethyl ester and for compound (iii) the 2-methylenebutandicarboxylic acid diethyl ester, which with the diethyl mesaconate ('Ej-2-methyl-but-2-endicarboxylic acid diethyl ester a preferred
- the compound of the formula (i), based on the sum of the compounds of the formula (i), of the formula (ii) and of the formula (iii), is in an amount of 50 to 100 wt .-% in the perfume mixture.
- This also applies to the particularly preferred compounds of the respective diethyl ester.
- mesaconic acid diethyl ester in at least 98.0% but above all also in 100.0% purity. This fragrance mixture with pure or almost pure Mesaconklathylester shows a particularly strong smell with pear note.
- the compound of the formula (i) is at least 8 in the fragrance mixture relative to the sum of the two compounds of the formula (ii) and the formula (iii) (compound of the formula (i)) to 1 (sum of the two compounds of the formula (ii) and the formula (iii)), particularly preferably in the ratio 9: 1 or with even greater proportion of the formula (i).
- These ratios also apply to the compound mixture of diethyl mesaconate to diethyl citraconate and diethyl itaconate. At higher proportions of Mesaconklaranmaschineranmaschineranmaschineranmaschineranmaschineranmaschineranmaschineranmaschineranmaschineranmaschineranmaschineranmaschineranmaschineranmaschineranmaschineranmaschineranmaschineranmaschineranmaschineranmaschineranmaschineranmaschineranmaschineranmaschineranmaschineranmaschineranmaschineranmaschineranmaschineranmaschineranmaschineranmaschineranmaschineranmaschineranmaschineranmaschineranmaschineranmaschineranmaschineranmaschineranmaschineranmaschineranmaschineranmaschineranmaschineranmaschineranmaschineranmaschineranmaschineranmaschineranmaschineranmaschineranmaschineranmaschineranmaschineran
- odour- like compounds such as 2,4-ethyldecadienoate (III)
- II 2,4-ethyldecadienoate
- the outstanding material properties such as solubility in customary cosmetic solvents, compatibility with other constituents of such products and the toxicological safety of the compound, which underline the particular suitability of the compound according to the invention for the stated purposes, should also be mentioned.
- Another advantage over the conventional fragrances with similar odor profiles (such as formula III) is its very low availability and production.
- the compounds of the formula (i), of the formula (ii) and / or of the formula (iii), based on the perfume mixture in an amount of from 0.001 to 99.999 wt. % contain.
- the compounds of the formula (i), of the formula (ii) and / or of the formula (iii), based on the perfume mixture in an amount of from 0.05 to 50 wt .-% together. This also applies to the particularly preferred compounds of the respective diethyl ester.
- the compounds of the formula (i), of the formula (ii) and / or of the formula (iii), based on the perfume mixture, in an amount of 1 to 30 wt. % contain.
- the mixtures may contain the compounds of the formula (i), of the formula (ii) and / or of the formula (iii) in general, or the ('E) -2-methyl-but Diethyl 2-endicarboxylic acid per se, or, the diethyl malonate in admixture with citraconic acid diethyl ester and diethyl itaconate in particular, in a sensorially effective amount of 0.001 to about 99.999 wt .-%, preferably in an amount of about 0.01 to about 90 Wt .-%, preferably in an amount of about 0.05 to about 50 wt .-% and particularly preferably in an amount of about 0.5 to about 25 wt .-%.
- the sum of 100% by weight then make up the fragrances and, if appropriate, solvents and / or preservatives in the case of fragrance mixtures. Depending on the application but also other additives can be added.
- FRAGRANCES The perfume mixtures according to the invention necessarily contain a further perfume, ie at least two perfume components, or consist of the isomer mixture of the compounds of formula (i), of formula (ii) and / or of formula (iii), and in particular (E -2-Methyl-but-2-endicarboxylic acid diethyl ester in a sensory effective amount with at least another perfume.
- fragrances are not used in binary or ternary mixtures, but as part of sophisticated complex mixtures that may contain 10, 20, 50, 100 or more fragrances in some very small amounts to give a particularly round odor profile.
- the present mixtures of the invention are to be understood, namely as a mixture of the mixture of the compounds of formula (i), the formula
- the perfume mixture described contains an arbitrarily large number of other perfumes selected from the group consisting of: (1) hydrocarbons; (2) aliphatic alcohols; (3) aliphatic aldehydes and their acetals; (4) aliphatic ketones and their oximes; (5) aliphatic sulfur compounds; (6) aliphatic nitriles; (7) esters of aliphatic carboxylic acids; (8) acyclic terpene alcohols; (9) acyclic terpene aldehydes and ketones; (10) cyclic terpene alcohols; (1 1) Cyclic terpene aldehydes and ketones;
- Extracts of natural raw materials This group stands for essential oils, concretes, absolues, resines, resinoids, balms, tinctures such as. B. amber tincture; Amyrisöl; Angelica seed oil; Angelica root oil; anise oil; Valerian oil; Basil oil; Tree moss absolute; Bay oil; Mugwort oil; Benzoeresin; Bergamot oil; Bee wax absolute; birch tar; Bitter almond oil; Savory oil; Buccoright oil; Cabreuvaöl; cade oil; calamus; camphor oil; Cananga oil; cardamom; Cascarillaöl; cassia; Cassie absolute; Beaver-absolue; Cederngeöl; cedarwood; cistus; citronella; lemon; copaiba balsam; Copaivabalsamöl; Coriander oil; costus root; Cuminöl; Cypress oil; Davanaöl; Dill herb oil; Dill seed oil; Eau de Brouts absolute; Oak
- hydrocarbons e.g. 3-carene; ⁇ -pinene; beta-pinene; a-terpinene; ⁇ -terpinene; p-cymene; bisabolene; camphene; caryophyllene; cedrene; farnesene; limonene; longifolene; myrcene; ocimene; valencene; (E, Z) -1, 3,5-undecatriene; styrene; diphenylmethane;
- Aliphatic alcohols e.g. hexanol; octanol; 3-octanol; 2,6-dimethylheptanol; 2-methyl-2-heptanol; 2-methyl-2-octanol; (E) -2-hexeno ⁇ ; (E) - and (j-3-hexenol; 1-octen-3-ol; mixture of 3,4,5,6,6-pentamethyl-3/4-hepten-2-ol and 3,5,6, 6-tetramethyl-4-methyleneheptan-2-ol; (E, Z) -2,6-nonadienol; 3,7-dimethyl-7-methoxyoctan-2-ol; 9-decenol; 10-undecenol; 4-methyl- 3-decen-5-ol;
- Aliphatic aldehydes and their acetals e.g. hexanal; heptanal; octanal; nonanal; decanal; undecanal; dodecanal; tridecanal; 2-methyloctanal; 2-methylnonanal; (Ej ⁇ -hexenal; (j-4-heptenal; 2,6-dimethyl-5-heptenal; 10-undecenal; (EM-decenal; 2-dodecenal; 2,6,10-trimethyl-9-undecenal; 2, 6,10-trimethyl-5,9-undecadienal; heptane-diethyl acetal; 1, 1-dimethoxy-2,2,5-trimethyl-4-hexene; citronellyloxyacetaldehyde; 1 - (1-methoxy-propoxy) - (E / Z) - 3-hexene;
- Aliphatic ketones and their oximes e.g. 2-heptanone; 2-octanone; 3- Octanone; 2-nonanone; 5-methyl-3-heptanone; 5-methyl-3-heptanone oxime; 2,4,4,7-tetramethyl-6-octen-3-one; 6-methyl-5-hepten-2-one;
- Aliphatic sulfur compounds such as e.g. 3-methylthio-hexanol; 3-Methylthiohexylacetat; 3-mercaptohexanol; 3-mercaptohexyl acetate; 3-mercaptohexyl butyrate; 3-acetylthiohexyl acetate; 1-Menthene-8-thiol;
- Aliphatic nitriles such as 2-nonenonitrile; 2-Undecen Textrenitril; 2-tridecenoic acid nitrile; 3,12-Tridecadien Acid nitrile; 3,7-dimethyl-2,6-octadiene-acid nitrile; 3,7-dimethyl-6-octen Aciditril; [48] esters of aliphatic carboxylic acids such as (E) - and (Z) -3-hexenylformate; ethylacetoacetate; isoamyl; hexyl acetate; 3,5,5-thmethylhexyl acetate; 3-methyl-2-butenyl acetate; ('Ej-2-hexenyl acetate, (E) - and (Z) -3-hexenyl acetate, octyl acetate, 3-octyl acetate, 1-octen-3-yl acetate,
- Acyclic terpene alcohols such. Citronellol; geraniol; nerol; linalool; Lavadulol; nerolidol; farnesol; tetrahydrolinalool; tetrahydrogeraniol; 2,6-dimethyl-7-octene-2-ol; 2,6-dimethyl octane-2-ol; 2-methyl-6-methylene-7-octen-2-ol; 2,6-dimethyl-5,7-octadien-2-ol; 2,6-dimethyl-3,5-octadiene-2-ol; 3,7-dimethyl-4,6-octadiene-3-ol; 3,7-dimethyl-1, 5,7-octatrien-3-ol 2,6-dimethyl-2,5,7-octathen-1-ol; as well as their formates, acetates, propionates, isobutyrates, but
- Acyclic terpene aldehydes and ketones such as. B. Geranial; neral; citronellal; 7-hydroxy-3,7-dimethyloctanal; 7-methoxy-3,7-dimethyloctanal; 2,6,10-thymethyl-9-undecenal; geranyl acetone; and the dimethyl and diethyl acetals of geranial, neral, 7-hydroxy-3,7-dimethyloctanal;
- Cyclic terpene alcohols such as Menthol; isopulegol; alpha-terpineol; Terpinenol-4; Menthane-8-ol; Menthan-1-ol; Menthane-7-ol; borneol; soborneol; linalool; monopoly; cedrol; ambrinol; Vetyverol; guaiol; as well as their formates, acetates, propionates, isobutyrates, butyrates, isovalerates, pentanoates, hexanoates, crotonates, tiglinates and 3-methyl-2-butenoates;
- Cyclic terpene aldehydes and ketones such as Eg menthone; Isomenthone; 8-mercaptomenthan-3-one; carvone; camphor; fenchon; alpha-ionone; beta-ionone; alpha-methylionone; beta-n-methylionone; alpha-isomethylionone; beta-isomethylionone; alpha-lron; alpha-damascone; beta-damascone; beta-damascenone; delta-damascone; gannnna-Dannascon; 1 - (2,4,4-Thmethyl-2-cyclohexene-1-yl) -2-butene-1-one; 1, 3,4,6,7,8a-hexahydro-1,1,5,5-tetramethyl-2H-2,4a-methanonaphthalene-8 (5H) -one; 2-methyl-4- (2,6, 6-trimethyl-1-cyclohexene
- Cyclic alcohols e.g. 4-tert-butylcyclohexanol; 3,3,5-thymethylcyclohexanol; 3-lsocamphylcyclohexanol; 2,6,9-trimethyl-Z2, Z5, E9-cyclododecathen-1-ol; 2-isobutyl-4-methyl tetrahydro-2H-pyran-4-ol;
- Thmethylcyclohexylmethanol 1 - (4-isopropylcyclohexyl) ethanol; 2-methyl-4- (2,2,3-thmethyl-3-cyclopent-1-yl) butanol; 2-methyl-4- (2,2,3-thmethyl-3-cyclopent-1-yl) -2-butene-1-ol; 2-ethyl-4- (2,2,3-trimethyl-3-cyclopent-1-yl) -2-butene-1-ol; 3-methyl-5- (2,2,3-trimethyl-3-cyclopent-1-yl) -pentan-2-ol; 3-methyl-5- (2,2,3-trimethyl-3-cyclopent-1-yl) -4-penten-2-ol; 3,3-dimethyl-5- (2,2,3-thmethyl-3-cyclopent-1-yl) -4-penten-2-ol; 1 - (2,2,6-thymethylcyclohexyl) pentan-3-ol; 1 - (2,2,6-
- Cyclic and cycloaliphatic ethers e.g. cineol; cedryl methyl ether; Cyclododecyl methyl ether; 1, 1-dimethoxycyclododecane;
- Cyclic and macrocyclic ketones e.g. 4-tert.-butylcyclohexanone; 2,2,5-trimethyl-5-pentylcyclopentanone; 2-heptylcyclopentanone; 2
- pentylcyclopentanone 2-hydroxy-3-methyl-2-cyclopentene-1-one; 3-methyl-cis-2-penten-1-yl-2-cyclopenten-1-one; 3-methyl-2-pentyl-2-cyclopentene-1-one; 3-methyl-4-cyclopentadecenone; 3-methyl-5-cyclopentadecenone; 3-methylcyclopentadecanone; 4- (1-ethoxyvinyl) -3,3,5,5-tetramethylcyclohexanone; 4-tert.-pentylcyclohexanone; 5 Cyclohexadecene-1-one; 6,7-dihydro-1,1,3,3,3-pentanethyl-4 (5H) -indanone; 8-cyclohexadecen-1-on; 9-cycloheptadecene-1-one; cyclopentadecanone; cyclohexadecanone;
- Cycloaliphatic ketones such as B. 1 - (3,3-dimethylcyclohexyl) -4-penten-1-one; 2,2-dimethyl-1 - (2,4-dimethyl-3-cyclohexene-1-yl) -1-propanone; 1 - (5,5-dimethyl-1-cyclohexene-1-yl) -4-penten-1-one; 2,3,8,8-tetramethyl-1,2,3,4,5,6,7,8-octahydro-2-naphthalenyl methyl ketone; Methyl-2,6,10-trimethyl-2,5,9-cyclododecatrienylketon; tert-butyl (2,4-dimethyl-3-cyclohexene-1-yl) ketone;
- esters of cyclic alcohols e.g. 2-tert-butylcyclohexyl acetate; 4-tert-butylcyclohexyl acetate; 2-tert-pentylcyclohexyl acetate; 4-tert-pentylcyclohexyl acetate; 3,3,5-Trimethylcyclohexylacetat; Decahydro-2-naphthyl acetate; 2-cyclopentylcyclopentyl crotonate; 3-pentyltetrahydro-2H-pyran-4-yl acetate; Decahydro-2,5,5,8-tetramethyl-2-naphthyl acetate; 4,7-methano-3a, 4,5,6,7,7a-hexahydro-5, and 6-indenyl acetate, respectively; 4,7-methano-3a, 4,5,6,7,7a-hexahydro-5, and 6-indenylprop
- esters of cycloaliphatic alcohols such as 1-cyclohexylethyl crotonate
- esters of cycloaliphatic carboxylic acids such as allyl-3-cyclohexylpropionate; Allylcyclohexyloxyacetat; cis and trans methyldihydrojasmonate; egg and trans methyl jasmonate; Methyl-2-hexyl-3-oxocyclopentanecarboxylate; Ethyl 2-ethyl-6,6-dimethyl-2-cyclohexene carboxylate; Ethyl 2,3,6,6-tetramethyl-2-cyclohexenecarboxylate; Ethyl 2-methyl-1,3-dioxolane-2-acetate;
- Araliphatic alcohols such as benzyl alcohol; 1-phenylethyl alcohol; 2-phenylethyl alcohol; 3-phenylpropanol; 2-phenylpropanol; 2-phenoxyethanol; 2,2- Dimethyl-3-phenylpropanol; 2,2-dimethyl-3- (3-nnethylphenyl) propanol; 1,1-dimethyl-2-phenylethyl alcohol; 1, 1-dimethyl-3-phenylpropanol; 1-ethyl-1-methyl-3-phenyl-propanol; 2-methyl-5-phenylpentanol; 3-methyl-5-phenylpentanol; 3-phenyl-2-propene-1-ol; 4-methoxybenzyl; 1 - (4-isopropylphenyl) ethanol;
- esters of araliphatic alcohols and aliphatic carboxylic acids e.g. benzyl acetate; benzylpropionate; benzyl isobutyrate; Benzylisovalerianat; 2-phenylethyl acetate; 2-phenylethyl propionate; 2-Phenylethylisobutyrat; 2-phenylethyl isovalerate; 1-phenylethyl acetate; alpha-Trichlormethylbenzylacetat; alpha, alpha-dimethylphenylethyl acetate; alpha, alpha-dimethylphenylethyl butyrate; Cinnannylacetat; 2-phenoxyethyl isobutyrate; 4-methoxybenzyl acetate;
- Araliphatic ethers e.g. 2-phenylethyl; 2-phenylethyl isoamyl ether; 2-phenylethyl-1-ethoxyethyl ether;
- phenylacetaldehyde phenylacetaldehyde
- phenylacetaldehyde Hydratropaaldehyddimethylacetal
- Phenylacetaldehydglycerinacetal 2,4,6-trimethyl-4-phenyl-1,3-dioxane
- 4,4a 5,9b-tetrahydroindeno [1,2-d] -m-dioxin
- 4,4a 5,9b-tetrahydro-2,4-dimethyl-indeno [1,2-d] -m-dioxin
- Aromatic and araliphatic aldehydes such as. B. benzaldehyde; phenylacetaldehyde; 3-phenylpropanal; Hydratropaaldehyd; 4-methylbenzaldehyde; 4-methylphenylacetaldehyde; 3- (4-ethylphenyl) -2,2-dimethylpropanal; 2-methyl-3- (4-isopropylphenyl) propanal; propanal, 2-methyl-3- (4-tert-butylphenyl); 2-methyl-3- (4-isobutylphenyl) propanal; 3- (4-tert-butylphenyl) propanal; cinnamic aldehyde; alpha-butylcinnamaldehyde; alpha-Amylzinntaldehyd; alpha-hexylcinnamaldehyde; 3-methyl-5-phenylpentanal; 4-methoxybenzaldehyde; 4-
- Aromatic and araliphatic ketones such as acetophenone; 4-methylacetophenone; 4-methoxyacetophenone; 4-tert-butyl-2,6-dimethylacetophenone; 4-phenyl-2-butanone; 4- (4-hydroxyphenyl) -2-butanone; 1 - (2-naphthalenyl) ethanone; 2- Benzofuranylethanon; (3-methyl-2-benzofuranyl) ethanone; benzophenone; 1, 1, 2,3,3,6-hexamethyl-5-indanylmethyl ketone; 6-tert-butyl-1, 1-dimethyl-4-indanyl-ethyl ketone; 1 - [2,3-dihydro-1, 1, 2,6-tetramethyl-3- (1-methylethyl) -1H-5-indenyl] ethanone; 5 ', 6', 7 ', 8'-tetrahydro-3', 5 ', 5', 6
- Aromatic and araliphatic carboxylic acids and their esters e.g. benzoic acid; phenylacetic acid; methylbenzoate; ethyl benzoate; hexyl benzoate; Benzyl benzoate; methyl phenylacetate; ethyl phenylacetate; geranyl phenylacetate; Phenylethyl phenylacetate; Methylcinnmat; ethylcinnamate; Benzyl; Phenylethylcinnamat; cinnamyl cinnamate; allyl phenoxyacetate; methyl salicylate; isoamyl; hexyl salicylate; cyclohexyl; Cis-3-hexenyl salicylate; benzyl; phenylethyl; Methyl-2,4-dihydroxy-3,6-dimethylbenzoate; Ethyl 3-phenylgly
- Nitrogen-containing aromatic compounds such as e.g. 2,4,6-trinitro-1,3-dimethyl-5-tert-butylbenzene; 3,5-dinitro-2,6-dimethyl-4-tert.-butylacetophenone; cinnamic acid; 3-methyl-5-phenyl-2-penten Aciditril; 3-methyl-5-phenylpentanenitrile; methyl anthranilate; Methyl N-methylanthranilate; Schiff's bases of methyl anthranilate with 7-hydroxy-3,7-dimethyloctanal, 2-methyl-3- (4-tert-butylphenyl) propanal or 2,4-dimethyl-3-cyclohexene carbaldehyde; 6-isopropylquinoline; 6-lsobutylchinolin; 6-sec.-butylquinoline; 2- (3-phenylpropyl) pyridine; indole; skatol; 2-methoxy-3
- Phenols, phenyl ethers and phenyl esters such as e.g. estragole; anethole; eugenol; Eugenylmethylether; isoeugenol; Isoeugenylmethylether; thymol; carvacrol; diphenyl ether; beta-naphthyl methyl ether; beta-Naphthylethylether; beta-naphthyl isobutyl ether; 1, 4-dimethoxybenzene; Eugenylacetat; 2-methoxy-4-methylphenol; 2-ethoxy-5- (1-propenyl) phenol; p-Kresylphenylacetat;
- Heterocyclic compounds such as 2,5-dimethyl-4-hydroxy-2H-furan-3-one; 2-ethyl-4-hydroxy-5-methyl-2H-furan-3-one; 3-hydroxy-2-methyl-4H-pyran-4-one; 2-ethyl-3-hydroxy-4H-pyran-4-one; [71] lactones such as 1, 4-octanolide; 3-methyl-1,4-octanolide; 1,4-nonanolide; 1, 4-decanolide; 8-decene-1,4-olide; 1,4-undecanolide; 1,4-dodecanolide; 1, 5-decanolide; 1, 5-dodecanolide; 4-methyl-1,4-decanolide; 1,15-pentadecanolide; cis and trans-1 1-pentadecene-1, 15-olide; cis- and trans-12-pentadecene-1, 15-olide; 1, 16-hexadecanolide; 9-hexa
- An eighth aspect of the present invention relates to perfume oils, cosmetics, dressings or detergents containing the inventive fragrance mixture described.
- a coating agent is to be understood as meaning all agents mentioned herein which do not fall under the group of perfume oils, cosmetics, or detergents and cleaners.
- these agents contain the inventive perfume mixture in amounts of from 0.05 to 5% by weight, based on the agent.
- the invention therefore relates both to vegetable oils, to cosmetic compositions, to the application materials, and to detergents and cleaners, including perfumed or perfumed products containing the compounds of the formula (i), of the formula (ii) and / or of the formula (iii) in general, or the (E) -2-methyl-but-2-endicarboxylic acid diethyl ester alone, or, the diethyl mesaconate in admixture with diethyl citraconate and diethyl itaconate in particular, or a corresponding perfume mixture as described in amounts of about 0.05 to about 5 wt .-%, based on the average, preferably in amounts of about 0.1 to about 3 wt .-% and in particular about 0.5 to about 2 wt%.
- Fragrance mixtures and perfume oils which contain the compounds of the formula (i), of the formula (ii) and / or of the formula (iii), or preferably (E -2-methyl-but-2-dicarboxylic acid diethyl ester or the mixture of diethyl mesaconate , Citraconsaurediethylester and Itaconsaurediethylester, can be used in liquid form, neat or diluted with a solvent for perfuming Suitable solvents are, for example, ethanol, isopropyl alcohol, diethylene glycol monoethyl ether, glycerol, propylene glycol, 1, 2-butylene glycol, dipropylene glycol, Diethyl phthalate, triethyl citrate, isopropyl myristate, etc.
- fragrance mixtures may be up to 90 wt .-%, preferably about 5 to about 70 wt .-%, in particular about 10 to about 50 wt .-% and particularly preferably about 15 to about 25 wt .-% of said Solvent included.
- perfume oils fragment mixtures containing compounds of the formula (i), of the formula (ii) and / or of the formula (iii), or preferably (E -2-methyl-but-2-ene).
- uch carriers can porous inorganic materials such as light sulfate, silica gels, zeolites , Gypsum, clays, clay granules, aerated concrete etc. or organic materials such as woods, cellulose-based substances, sugars or plastics such as PVC, polyvinyl acetates or polyurethanes.
- perfume oils or perfume mixtures of the invention microencapsulated, spray-dried, as an inclusion complex or as an extrusion product and to add in this form to the (preliminary) product to be perfumed.
- perfume oils or perfume mixtures modified in this way are further optimized in some cases by so-called "coating" with suitable materials with a view to a more targeted release of fragrance, for which purpose preferably waxy plastics such as polyvinyl alcohol are used.
- suitable materials for which purpose preferably waxy plastics such as polyvinyl alcohol are used.
- the microencapsulation of the perfume oils or perfume mixtures of the invention can be carried out, for example, by the so-called coacervation method with the aid of capsule materials, for example of polyurethane-type substances or soft gelatin.
- the spray-dried perfume oils can be prepared, for example, by spray-drying a perfume oil-containing emulsion or dispersion, it being possible to use as starches modified starches, proteins, dextrin and vegetable gums.
- Inclusion complexes can be prepared, for example, by incorporating dispersions of the perfume oil and cyclodextrins or urea derivatives into a suitable solvent, eg, water.
- Extrusion products can be made by fusing the perfume oils with a suitable waxy substance and by extrusion with subsequent solidification, optionally in a suitable solvent, for example isopropyl alcohol.
- the cosmetic compositions and personal care products according to the invention can be used in addition to the compounds of the formula (i), the formula (ii) and / or the formula (iii), or preferably ('Ej-2-methyl-but-2-endicarboxylic acid diethyl ester, or the mixture of diethyl malonate, diethyl citraconate and diethyl itaconate, or the perfume mixtures containing these compounds or mixtures contain further typical auxiliaries and additives, such as the mild surfactants, oil bodies, emulsifiers, pearlescent waxes, bodying agents, thickeners, superfatting agents, stabilizers, polymers mentioned below, Silicone compounds, fats, waxes, lecithins, phospholipids, UV protection factors, humectants, biogenic agents, antioxidants, deodorants, antiperspirants, antidandruff agents, film formers, swelling agents, insect repellents, self-tanning agents, tyrosine inhibitors (depig
- cosmetic agents are used interchangeably with each other and only assume that the agents are all a sensory effective amount of the compounds of formula (i), formula (ii) and / or Formula (iii) or preferably (E -2-methyl-but-2- diethyl endicarboxylate, or the mixture of diethyl mesaconate, citraconic acid diethyl ester and diethyl itaconate, or a fragrance mixture containing these diesters.
- Preferred additives are mentioned below.
- Surfactants which may be present are anionic, nonionic, cationic and / or amphoteric or zwitterionic surfactants, the proportion of which in the compositions is usually from about 1 to 70, preferably from 5 to 50, and in particular from 10 to 30,% by weight.
- anionic surfactants are soaps, alkylbenzenesulfonates, alkanesulfonates, olefinsulfonates, alkyl ether sulfonates, glycerol ether sulfonates, ⁇ -methyl ester sulfonates, sulfo fatty acids, alkyl sulfates, alkyl ether sulfates, glycerol ether sulfates, fatty acid ether sulfates, hydroxy mixed ether sulfates, monoglyceride (ether) sulfates, fatty acid amide (ether ) sulfates, mono- and dialkylsulfosuccinates, mono- and dialkylsulfosuccinamates, sulfotriglycerides, amide soaps, ether carboxylic acids and their salts, fatty acid isethionates, fatty acid sarcosinates,
- anionic surfactants contain polyglycol ether chains, these may have a conventional, but preferably a narrow homolog distribution.
- Typical examples of nonionic surfactants are fatty alcohol polyglycol ethers, alkylphenol polyglycol ethers, fatty acid polyglycol ethers, fatty acid amide polyglycol ethers, fatty amine polyglycol ethers, alkoxylated triglycerides, mixed ethers, optionally partially oxidized alk (en) yloligoglycosides or glucuronic acid derivatives, fatty acid N-alkylglucamides, protein hydrolysates (especially wheat-based vegetable products).
- Nonionic surfactants contain polyglycol ether chains, these may have a conventional, but preferably a narrow homolog distribution.
- Typical examples of cationic surfactants are quaternary ammonium compounds such as dimethyl distearyl ammonium chloride, and ester quats, especially quaternized fatty acid trialkanolamine ester salts.
- typical Examples of amphoteric or zwitterionic surfactants are alkylbetaines, alkylamidobetaines, aminopropionates, aminoglycinates, imidazolinium betaines and sulfobetaines.
- surfactants mentioned are exclusively known compounds.
- particularly suitable mild, ie particularly skin-friendly surfactants are fatty alcohol polyglycol ether sulfates, monoglyceride sulfates, mono- and / or dialkyl sulfosuccinates, fatty acid isethionates, fatty acid sarcosinates, fatty acid taurides, fatty acid glutamates, ⁇ -olefinsulfonates, ether carboxylic acids, alkyl oligoglucosides, fatty acid glucamides, alkylamidobetaines, amphoacetals and / or protein fatty acid condensates, the latter preferably based on wheat proteins.
- oil bodies are Guerbet alcohols based on fatty alcohols having 6 to 18, preferably 8 to 10 carbon atoms, esters of linear C6-C22 fatty acids with linear or branched C6-C22 fatty alcohols or esters of branched C6-C13 carboxylic acids with linear or branched C6-C22 fatty alcohols, for example myristyl myristate, myristyl palmitate, myristyl stearate, Myristylisostearat, myristyl, Myristylbehenat, Myristylerucat, cetyl myristate, cetyl palmitate, cetyl stearate, Cetylisostearat, cetyl oleate, cetyl behenate, Cetylerucat, Stearylmyristat, stearyl palmitate, stearyl stearate, Stearylisostearat, stearyl oleate, stearyl behenate, Stearyl
- esters of linear C6-C22 fatty acids with branched alcohols in particular 2-ethylhexanol
- esters of C18-C38-alkylhydroxycarboxylic acids with linear or branched C6-C22 fatty alcohols in particular dioctyl maleate
- esters of linear and / or branched fatty acids with polyhydric alcohols such as, for example, propylene glycol, dimerdiol or trimer triol
- polyhydric alcohols such as, for example, propylene glycol, dimerdiol or trimer triol
- Guerbet alcohols triglycerides based on CG-CI O fatty acids
- esters of C6-C22 Fatty alcohols and / or Guerbet alcohols with aromatic carboxylic acids in particular benzoic acid
- Emulsifiers are, for example, nonionic surfactants from at least one of the following groups:
- alkyl and / or alkenyl oligoglycosides having 8 to 22 carbon atoms in the alk (en) yl radical and their ethoxylated analogs;
- Adducts of 1 to 15 moles of ethylene oxide with castor oil and / or hydrogenated castor oil Adducts of 1 to 15 moles of ethylene oxide with castor oil and / or hydrogenated castor oil;
- Adducts of 15 to 60 moles of ethylene oxide with castor oil and / or hydrogenated castor oil Adducts of 15 to 60 moles of ethylene oxide with castor oil and / or hydrogenated castor oil;
- Block copolymers e.g. Polyethylene glycol-30 dipolyhydroxystearates
- Polymer emulsifiers e.g. Pemulen types (TR-1, TR-2) from Goodrich or Cosmedia® SP from Cognis;
- Alkoxylates The addition products of ethylene oxide and / or of propylene oxide onto fatty alcohols, fatty acids, alkylphenols or castor oil are known, commercially available products. These are homolog mixtures whose mean degree of alkoxylation corresponds to the ratio of the amounts of ethylene oxide and / or propylene oxide and substrate with which the addition reaction is carried out. C12 / 18 fatty acid mono- and diesters of addition products of ethylene oxide with glycerol are known as refatting agents for cosmetic preparations.
- Alkyl and / or alkenyl oligoglycoside Alkyl and / or alkenyl oligoglycosides, their preparation and their use are known in the art.
- glycoside radical both monoglycosides in which a cyclic sugar residue is glycosidically linked to the fatty alcohol and oligomeric glycosides having a degree of oligomerization of preferably approximately 8 are suitable.
- the degree of oligomerization is a statistical mean, which is based on a homolog distribution typical for such technical products.
- Partial glycerides Typical examples of suitable partial glycerides are hydroxystearic acid monoglyceride, hydroxystearic acid diglyceride, isostearic acid monoglyceride, isostearic acid diglyceride, oleic acid monoglyceride, oleic acid diglyceride, ricinoleic acid glyceride, ricinoleic acid diglyceride,
- sorbitan esters are sorbitan monoisostearate, sorbitan sesquiisostearate, sorbitan diisostearate, sorbitan triisostearate,
- Polyglycerol esters Typical examples of suitable polyglycerol esters are polyglyceryl-2 dipolyhydroxystearates (Dehymuls® PGPH), polyglycerol-3-diisostearates (Lameform® TGI), polyglyceryl-4 isostearates (Isolan® Gl 34), polyglyceryl-3 oleates, diisostearoyl polyglyceryl -3 Diisostearate (Isolan® PDI), Polyglyceryl-3 Methylglucose Distearate (Tego Care® 450), Polyglyceryl-3 Beeswax (Cera Bellina®), Polyglyceryl-4 Caprate (Polyglycerol Caprate T2010 / 90), Polyglyceryl-3 Cetyl Ether (Chimexane ® NL), polyglyceryl-3 distearate (Cremophor® GS 32) and polyglyceryl polyricinoleate (Admul
- polystyrene resin examples include the mono-, di- and triesters of trimethylolpropane or pentaerythritol with lauric acid, coconut fatty acid, tallow fatty acid, palmitic acid, stearic acid, oleic acid, behenic acid and the like, which are optionally reacted with from 1 to 30 mol of ethylene oxide.
- Anionic emulsifiers are aliphatic fatty acids having 12 to 22 carbon atoms, such as palmitic acid, stearic acid or behenic acid, and dicarboxylic acids having 12 to 22 carbon atoms, such as azelaic acid or sebacic acid.
- zwitterionic surfactants can be used as emulsifiers.
- Zwitterionic surfactants are those surface-active compounds which carry at least one quaternary ammonium group and at least one carboxylate and one sulfonate group in the molecule.
- Particularly suitable zwitterionic surfactants are the so-called betaines such as N-alkyl-N, N-dimethylammonium glycinates, for example cocoalkyldimethylammonium glycinate, N-acylaminopropyl-N, N-dimethylammonium glycinates, for example cocoacylaminopropyldimethylammonium glycinate, and 2-alkyl-3-carboxylmethyl-3 Hydroxyethylimidazoline having in each case 8 to 18 carbon atoms in the alkyl or acyl group and the Kokosacylamino- ethylhydroxyethylcarboxymethylglycinat.
- betaines such as N-alkyl-N, N-dimethylammonium glycinates, for example cocoalkyldimethylammonium glycinate, N-acylaminopropyl-N, N-dimethylammonium glycinates,
- emulsifiers are used as suitable emulsifiers.
- Ampholytic surfactants are understood as meaning those surface-active compounds which contain, in addition to a ceria or acyl group in the molecule, at least one free amino group and at least one -COOH or -SOsH group and are capable of forming internal salts.
- ampholytic surfactants are N-alkylglycines, N-alkylpropionic acids, N-alkylaminobutyric acids, N-alkyliminodipropionic acids, N-hydroxyethyl-N-alkylamidopropylglycines, N-alkyltaurines, N-alkylsarcosines, 2-alkylaminopropionic acids and alkylaminoacetic acids each about 8 to 18 carbon atoms in the alkyl group.
- Particularly preferred ampholytic surfactants are N-cocoalkylaminopropionate, cocoacylaminoethylaminopropionate and C12 / 18 acylsarcosine.
- cationic surfactants are also suitable as emulsifiers, those of the esterquat type, preferably methyl-quaternized difatty acid triethanolamine ester salts, being particularly preferred.
- Fats and waxes Typical examples of fats are glycerides, ie solid or liquid vegetable or animal products consisting essentially of mixed glycerol esters of higher fatty acids, waxes include natural waxes such as candelilla wax, carnauba wax, Japan wax, Esparto grass wax, Cork wax, guaruma wax, rice germ oil wax, sugarcane wax, ouricury wax, montan wax, beeswax, shellac wax, spermaceti, lanolin (wool wax), crepe fat, ceresin, ozokerite (groundwax), petrolatum, paraffin waxes, microwaxes; chemically modified waxes (hard waxes), such as montan ester waxes, Sasol waxes, hydrogenated jojoba waxes and synthetic waxes, such as polyalkylene waxes and polyethylene glycol waxes in question.
- waxes include natural waxes such as candelilla wax, carna
- lecithins In addition to the fats come as additives and fat-like substances such as lecithins and phospholipids in question.
- lecithin those skilled in the art will understand those glycerophospholipids which are formed from fatty acids, glycerol, phosphoric acid and choline by esterification.
- Lecithins are therefore often referred to in the art as phosphatidylcholines (PC).
- PC phosphatidylcholines
- cephalins which are also referred to as phosphatidic acids and derivatives of 1, 2-diacyl-sn-glycerol-3-phosphoric acids.
- phospholipids usually mono- and preferably diesters of Phosphoric acid with glycerol (glycerol phosphates), which are generally expected to be the fats.
- glycerol phosphates glycerol phosphates
- sphingosines or sphingolipids are also suitable.
- Pearlescent Waxes Suitable pearlescent waxes are, for example: alkylene glycol esters, especially ethylene glycol distearate; Fatty acid alkanolamide, especially coconut fatty acid diethanolamide; Partial glycerides, especially stearic acid monoglyceride; Esters of polybasic, optionally hydroxy-substituted carboxylic acids with fatty alcohols having 6 to 22 carbon atoms, especially long-chain esters of tartaric acid; Fatty substances, such as fatty alcohols, fatty ketones, fatty aldehydes, fatty ethers and fatty carbonates, which in total have at least 24 carbon atoms, especially lauron and distearyl ether; Fatty acids such as stearic acid, hydroxystearic acid or behenic acid, ring-opening products of olefin epoxides having 12 to 22 carbon atoms with fatty alcohols having 12 to 22 carbon atoms and / or polyols having 2 to
- Coolants are compounds that create a feeling of coldness on the skin. In general, these are menthol compounds which - in addition to the main body menthol itself - for example selected from the group formed by menthol methyl ether, menthone glyceryl acetal (FEMA GRAS 1 3807), Menthone glyceryl ketal (FEMA GRAS 3808) , Menthyl Lactate (FEMA GRAS 3748), Menthol Ethylene Glycol Carbonate (FEMA GRAS 3805), Menthol Propylene Glycol Carbonate (FEMA GRAS 3806), Menthyl N -ethyloxamate, Monomethyl Succinate (FEMA GRAS 3810), Monomenthyl Glutamate (FEMA GRAS 4006) , Menthoxy-1,2-propanediol (FEMA GRAS 3784), menthoxy-2-methyl-1,2-propanediol (FEMA GRAS 3849) and the menthane carboxylic
- FEMA Food and Extracts Manufacturers Association
- GRAS GRAS is defined as "Generally Regarded As Safe”.
- a FEMA GRAS designation means that the substance identified in this way is tested according to the standard method and considered to be toxicologically harmless.
- Monomenthyl succinate FEMA GRAS 3810
- Both the succinate and the analogous monomenthyl glutarate FEMA GRAS 4006 are important representatives of monomethyl esters based on di- and polycarboxylic acids:
- FEMA GRAS 3805 Frescolate® MGC
- FEMA GRAS 3784 Frescolat® MPC
- FEMA GRAS 3849 menthol 2-methyl-1,2-propanediol carbonates
- FEMA GRAS 3807 Menthone glyceryl acetal
- FEMA GRAS 3808 Menthone glyceryl ketal
- Frescolat® MGA Menthone glycerol acetal / ketal and the menthyl lactates and menthol ethylene glycol carbonates or menthol propylene glycol carbonate w, which the applicant has designated Frescolat.RTM. MGA, Frescolat.RTM. ML, Frecolat.RTM. MGC and Frescolat, have proven to be particularly advantageous among these substances ® MPC sells.
- menthol compounds were first developed that have a C-C bond in the 3-position and from which a number of representatives can also be used. These substances are generally referred to as WS types.
- Base is a menthol derivative in which the hydroxyl is replaced by a carboxyl group (WS-1). From this structure, all other types of WS are derived, such as the preferred species WS-3, WS-4, WS-5, WS-12, WS-14 and WS-30.
- Bodying agents and thickeners As consistency factors, preference is given to fatty alcohols or hydroxy fatty alcohols having 12 to 22 and preferably 16 to 18 carbon atoms and, in addition, partial glycerides, fatty acids or hydroxy fatty acids. Preference is given to a combination of these substances with alkyl oligoglucosides and / or fatty acid N-methylglucamides of the same chain length and / or polyglycerol poly-12-hydroxystearates.
- Suitable thickeners are, for example, Aerosil types (hydrophilic silicic acids), polysaccharides, in particular xanthan gum, guar guar, agar agar, alginates and tyloses, carboxymethyl cellulose and hydroxyethyl and hydroxypropyl cellulose, and also higher molecular weight polyethylene glycol mono- and diesters of fatty acids, Polyacrylates, (eg Carbopole® and Pemulen types from Goodrich, Synthalene® from Sigma, Keltrol types from Kelco, sepiolite types from Seppic, Salcare types from Allied Colloids), polyacrylamides, polymers, polyvinyl alcohol, and polyvinylpyrrolidone.
- Aerosil types hydrophilic silicic acids
- polysaccharides in particular xanthan gum, guar guar, agar agar, alginates and tyloses, carboxymethyl cellulose and hydroxyethyl and hydroxypropy
- Bentonites such as e.g. Bentone® Gel VS-5PC (Rheox), which is a mixture of cyclopentasiloxane, disteardimonium hectorite and propylene carbonate.
- surfactants such as, for example, ethoxylated fatty acid glycerides, esters of fatty acids with polyols, for example pentaerythritol or trimethylolpropane, fatty alcohol ethoxylates with narrow homolog distribution or alkyl oligoglucosides and also electrolytes, such as common salt and ammonium chloride.
- Superfatting agents may be substances such as lanolin and lecithin, as well as polyethoxylated or acylated lanolin and lecithin derivatives, polyol fatty acid esters, monoglycerides and fatty acid alkanolamides, the latter also serving as foam stabilizers.
- Suitable cationic polymers are, for example, cationic cellulose derivatives, such as a quaternized hydroxyethylcellulose available under the name Polymer JR 400® from Amerchol, cationic starch, copolymers of diallylammonium salts and acrylamides, quaternized vinylpyrrolidone / vinylimidazole polymers, such as Luviquat® (BASF), condensation products of polyglycols and amines, quaternized collagen polypeptides, such as Lauryldimonium Hydroxypropyl Hydrolyzed Collagen (Lamequat®L / Grünau), quaternized wheat polypeptides, polyethyleneimine, cationic silicone polymers, such as amodimethicones, copolymers of adipic acid and dimethylaminohydroxyprop
- anionic, zwitterionic, amphoteric and nonionic polymers are vinyl acetate / crotonic acid copolymers
- Vinylpyrrolidone / vinyl acrylate copolymers vinyl acetate / butyl maleate / isobornyl acrylate copolymers, methyl vinyl ether / maleic anhydride copolymers and their esters, uncrosslinked and polyols crosslinked polyacrylic acids, acrylamidopropyltrimethylammonium chloride / acrylate copolymers, octylacrylamide / methylmethacrylate / tert. butylaminoethyl methacrylate / 2-hydroxypropyl methacrylate copolymers,
- Silicone compounds are, for example, dimethylpolysiloxanes, methylphenylpolysiloxanes, cyclic silicones and amino, fatty acid, alcohol, polyether, epoxy, fluorine, glycoside and / or alkyl-modified Silicone compounds which may be both liquid and resinous at room temperature. Also suitable are simethicones, which are mixtures of dimethicones having an average chain length of from 200 to 300 dimethylsiloxane units and hydrogenated silicates.
- UV sun protection factors mean, for example, liquid or crystalline organic substances (light protection filters) which are able to absorb ultraviolet rays and absorb the absorbed energy in the form of longer-wave radiation, e.g. Heat again.
- the UV sunscreen factors are present in amounts of 0.1 to 5 and preferably 0.2 to 1 wt .-%.
- UVB filters can be oil-soluble or water-soluble. As oil-soluble substances are e.g. to call:
- 4-aminobenzoic acid derivatives preferably 2-ethylhexyl 4- (dimethylamino) benzoate, 2-octyl 4- (dimethylamino) benzoate and 4- (dimethylamino) benzoic acid amyl ester;
- Esters of cinnamic acid preferably 4-methoxycinnamic acid 2-ethylhexyl ester, 4-methoxycinnamic acid propyl ester, 4-methoxycinnamic acid isoamyl ester 2-cyano-3,3-phenylcinnamic acid 2-ethylhexyl ester (octocrylene);
- Esters of salicylic acid preferably 2-ethylhexyl salicylate, 4-iso-propylbenzyl salicylate, homomenthyl salicylate;
- benzophenone preferably 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-methoxy-4'-methylbenzophenone, 2,2'-dihydroxy-4-methoxybenzophenone;
- Esters of benzalmalonic acid preferably di-2-ethylhexyl 4-methoxybenzmalonate
- Triazine derivatives e.g. 2,4,6-trianilino (p-carbo-2'-ethyl-1'-hexyloxy) -1, 3,5-triazine and octyl triazone or dioctyl butamido triazone (Uvasorb® HEB);
- Propane-1,3-diones e.g. 1 - (4-tert-butylphenyl) -3- (4'-methoxyphenyl) propane-1,3-dione;
- Sulphonic acid derivatives of benzophenones preferably 2-hydroxy-4-methoxybenzo-phenone-5-sulphonic acid and their salts;
- Sulfonic acid derivatives of the 3-benzylidene camphor e.g. 4- (2-Oxo-3-bornylidenemethyl) benzenesulfonic acid and 2-methyl-5- (2-oxo-3-bornylidene) sulfonic acid and salts thereof.
- UV-A filter in particular derivatives of benzoylmethane in question, such as 1 - (4'-tert-butylphenyl) -3- (4'-methoxyphenyl) propane-1, 3-dione, 4-tert Butyl 4'-methoxydibenzoylmethane (Parsol® 1789), 2- (4-diethylamino-2-hydroxybenzoyl) benzoic acid hexyl ester (Uvinul® A Plus), 1-phenyl-3- (4'-isopropylphenyl) -propane -1, 3-dione and enamine compounds.
- the UV-A and UV-B filters can also be used in mixtures.
- Particularly favorable combinations consist of the derivatives of benzoylmethane, e.g. 4-tert-butyl-4'-methoxydibenzoylmethane (Parsol® 1789) and 2-cyano-3,3-phenylcinnamic acid 2-ethylhexyl ester (octocrylene) in combination with ester of cinnamic acid, preferably 2-ethylhexyl 4-methoxycinnamate and / or 4-Methoxycinntklarepropylester and / or 4-Methoxycinntklareisoamylester.
- water-soluble filters e.g. 2-phenylbenzimidazole-5-sulfonic acid and their alkali, alkaline earth, ammonium, alkylammonium, alkanolammonium and glucammonium combined.
- insoluble photoprotective pigments namely finely dispersed metal oxides or salts
- suitable metal oxides are in particular zinc oxide and titanium dioxide and, in addition, oxides of iron, zirconium, silicon, manganese, aluminum and cerium and mixtures thereof.
- salts silicates (talc), barium sulfate or zinc stearate can be used.
- the oxides and salts are used in the form of the pigments for skin-care and skin-protecting emulsions and decorative cosmetics.
- the particles should have an average diameter of less than 100 nm, preferably between 5 and 50 nm and in particular between 15 and 30 nm.
- the pigments may have a spherical shape, but it is also possible to use those particles which have an ellipsoidal or otherwise deviating shape from the spherical shape.
- the pigments can also be surface-treated, ie hydrophilized or hydrophobized.
- Typical examples are coated titanium dioxides, such as titanium dioxide T 805 (Degussa) or Eusolex® T2000, Eusolex® T, Eusolex® T-ECO, Eusolex® TS, Eusolex® T-Aqua, Eusolex® T-45D (all Merck), Uvinul T1O2 (BASF).
- Suitable hydrophobic coating agents are in particular silicones and in particular trialkoxyoctylsilanes or simethicones.
- sunscreens so-called micro- or nanopigments are preferably used.
- micronized zinc oxide such as Z-COTE® or Z-COTE HP1® is used.
- Humectants serve to further optimize the sensory properties of the composition and to regulate the moisture of the skin. At the same time, the low-temperature stability of the preparations according to the invention, in particular in the case of emulsions, is increased.
- the humectants are usually contained in an amount of 0.1 to 15 wt .-%, preferably 1 to 10 wt .-%, and especially 5 to 10 wt .-%.
- Biogenic agents and antioxidants include, for example, tocopherol, tocopherol acetate, tocopherol palmitate, ascorbic acid, (deoxy) ribonucleic acid and their fragmentation products, ⁇ -glucans, retinol, bisabolol, allantoin, phytantriol, panthenol, AHA acids, amino acids, ceramides , Pseudoceramides, essential oils, plant extracts, such as Prunus extract, Bambaranussex Install and vitamin complexes to understand.
- Antioxidants interrupt the photochemical reaction chain, which is triggered when UV radiation penetrates the skin.
- Typical examples are amino acids (eg glycine, histidine, tyrosine, tryptophan) and their derivatives, imidazoles (eg urocaninic acid) and their derivatives, peptides such as D, L-carnosine, D-carnosine, L-carnosine and their derivatives (eg anserine) , Carotenoids, carotenes (eg ⁇ -carotene, ⁇ -carotene, lycopene) and their derivatives, chlorogenic acid and its derivatives, lipoic acid and derivatives thereof (eg dihydrolipoic acid), aurothioglucose, propylthiouracil and other thiols (eg thioredoxin, glutathione, cysteine, cystine, Cystamine and its glycosyl, N-acetyl, methyl, ethyl,
- Deodorants and antimicrobials Cosmetic deodorants (deodorants) counteract, mask or eliminate body odors. Body odors are caused by the action of skin bacteria on apocrine sweat, forming unpleasant-smelling degradation products. Accordingly, deodorants contain active ingredients which act as anti-sprouting agents, enzyme inhibitors, odor absorbers or odor maskers.
- Germ-inhibiting agents In principle, all substances which are active against Gram-positive bacteria are suitable as germ-inhibiting agents.
- Enzyme inhibitors are, for example, esterase inhibitors. These are preferably trialkyl citrates such as trimethyl citrate, tripropyl citrate, triisopropyl citrate, tributyl citrate and in particular triethyl citrate (Hydagen® CAT). The substances inhibit the enzyme activity and thereby reduce odors.
- esterase inhibitors include sterol sulphates or phosphates, such as, for example, lanosterol, Cholesterol, campesterol, stigmasterol and sitosterol sulfate or phosphate, dicarboxylic acids and their esters, such as, for example, glutaric acid, glutaric acid monoethyl ester, glutaric acid diethyl ester, adipic acid,
- Odor absorbers are substances that absorb and largely retain odor-forming compounds. They reduce the partial pressure of the individual components and thus also reduce their propagation speed. It is important that perfume must remain unimpaired. Odor absorbers have no activity against bacteria. They contain, for example, as a main component of a complex zinc salt of ricinoleic acid or special, largely odorless fragrances, which are known in the art as "fixatives", such. B. Extracts of Labdanum or Styrax or certain Abietinklarivate. Odor maskers are fragrances or perfume oils which, in addition to their function as odor maskers, give the deodorants their respective scent. Examples of perfume oils are mixtures of natural and synthetic fragrances.
- Natural fragrances are extracts of flowers, stems and leaves, fruits, fruit peel, roots, woods, herbs and grasses, needles and twigs, as well as resins and balsams. Furthermore, animal raw materials come into question, such as civet and Castoreum.
- Typical synthetic fragrance compounds are ester type products, ethers, aldehydes, ketones, alcohols and hydrocarbons.
- Fragrance compounds of the ester type are, for example, benzyl acetate, p-tert-butylcyclohexyl acetate, linalyl acetate, phenylethyl acetate, linalyl benzoate, benzyl formate, allylcyclohexyl propionate, styrallyl propionate and benzyl salicylate.
- the ethers include, for example, benzyl ethyl ether, to the aldehydes, for example, the linear alkanals having 8 to 18 carbon atoms, citral, citronellal, citronellyloxyacetaldehyde, cyclamen aldehyde, hydroxycitronellal, lilial and bourgeonal, to the ketones such as the ionone and methylcedrylketone to the alcohols anethole, Citronellol, eugenol, isoeugenol, geraniol, linalool, phenylethyl alcohol and terpineol belong to the hydrocarbons mainly the terpenes and balms.
- benzyl ethyl ether to the aldehydes, for example, the linear alkanals having 8 to 18 carbon atoms, citral, citronellal, citronellyloxyacetaldehyde, cyclamen al
- fragrance oils are suitable as perfume oils, such as sage oil, camomile oil, clove oil, lemon balm oil, mint oil, cinnamon oil, lime blossom oil, juniper berry oil, vetiver oil, oliban oil, galbanum oil, labdanum oil and lavandinol.
- bergamot oil dihydromyrcenol, lilial, lyral, citronellol, phenylethyl alcohol, ⁇ -hexylcinnamaldehyde, geraniol, benzylacetone, cyclamen aldehyde, linalool, Boisambrene Forte, Ambroxan, indole, hedione, Sandelice, citron oil, tangerine oil, orange oil, Allylamylglycolat, Cyclovertal, lavandinol, Muscat Sage oil, ⁇ -damascone, geranium oil Bourbon, cyclohexyl salicylate, Vertof ix Coeur, Iso-E-Super, fixolide NP, Evernyl, Iraldein gamma, phenylacetic acid, geranyl acetate, benzyl acetate, rose oxide, romilate, irot
- Antiperspirants reduce the formation of sweat by influencing the activity of the eccrine sweat glands, thus counteracting underarm wetness and body odor.
- Aqueous or anhydrous formulations of antiperspirants typically contain the following ingredients:
- auxiliaries such as B. thickener or complexing agent and / or
- non-aqueous solvents such as ethanol, propylene glycol and / or glycerol.
- Salts of aluminum, zirconium or zinc are especially suitable as astringent antiperspirant active ingredients.
- suitable antiperspirant active ingredients are, for example, aluminum chloride, aluminum chlorohydrate, aluminum dichlorohydrate, aluminum sesquichlorohydrate and their complex compounds z. With propylene glycol-1, 2.
- antiperspirants may contain customary oil-soluble and water-soluble adjuvants in smaller amounts.
- oil-soluble auxiliaries may be, for example:
- Usual water-soluble additives are e.g. Preservatives, water-soluble fragrances, pH adjusters, e.g. Buffer mixtures, water-soluble thickeners, e.g. water-soluble natural or synthetic polymers such as e.g. Xanthan gum, hydroxyethyl cellulose, polyvinyl pyrrolidone or high molecular weight polyethylene oxides.
- Film former Common film formers are, for example, chitosan, microcrystalline chitosan, quaternized chitosan, polyvinylpyrrolidone, vinylpyrrolidone-vinyl acetate copolymers, polymers of the acrylic acid series, quaternary cellulose derivatives, collagen, hyaluronic acid and salts thereof and similar compounds.
- Anti-dandruff agents are Pirocton olamine (1-hydroxy-4-methyl-6- (2,4,4-trimethylpentyl) -2- (1H) -pyridinone monoethanolamine salt), Baypival® (climbazole), Ketoconazole®, (4-Acetyl-1 - ⁇ -4- [2- (2,4-dichlorophenyl) r-2- (1 H -imidazol-1-ylmethyl) -1,3-dioxylan-c-4-ylmethoxyphenyl ⁇ piperazine, ketoconazole, Elubiol, Selenium Disulfide, Sulfur Colloidal, Sulfur Polyethylene Glycol Sorbitan Mono Oleate, Sulfur Rizinol Polyethoxylate, Schweltecker Distillates, Salicylic Acid (or in Combination with Hexachlorophene), Undeoxy Lactic Acid Monoethanolamide Sulfosuccinate Na Salt, Lamepon® UD
- Swelling agent The swelling agent used for aqueous phases can be montmorillonites, clay minerals, pemulen and alkyl-modified carbopol types (Goodrich). Further suitable polymers or swelling agents can be reviewed by R. Lochhead in Cosm.Toil. 108, 95 (1993).
- Suitable insect repellents are N, N-diethyl-m-toluamide, 1, 2-pentanediol or ethyl butylacetylaminopropionate.
- As a self-tanner dihydroxyacetone is suitable.
- Tyrosinhinbitoren that prevent the formation of melanin and find application in depigmenting, for example, arbutin, ferulic acid, kojic acid, coumaric acid and ascorbic acid (vitamin C) come into question.
- Toothpastes or toothpastes are generally understood gel or pasty preparations of water, thickeners, humectants, abrasive or cleaning articles, surfactants, sweeteners, flavorings, deodorants and active ingredients against oral and dental diseases.
- all the usual cleaning body such as. As chalk, dicalcium phosphate, insoluble sodium metaphosphate, aluminum silicates, calcium pyrophosphate, finely divided resins, silicas, alumina and alumina trihydrate are used.
- Particularly suitable cleaning bodies for the toothpastes according to the invention are, above all, finely divided xerogel silicas, hydrogel silicas, precipitated silicas, alumina trihydrate and finely divided alpha alumina or mixtures of these cleansers in amounts of from 15 to 40% by weight of the toothpaste.
- the humectants are mainly low molecular weight polyethylene glycols, glycerol, sorbitol or mixtures of these products in amounts up to 50 wt .-% in question.
- the known thickeners are the thickening, finely divided gel silicas and hydrocolloids, such as.
- the oral and dental care products can be used in particular surface-active substances, preferably anionic and nonionic high-foaming surfactants, such as the substances mentioned above, but especially alkyl ether sulfate salts, alkyl polyglucosides and mixtures thereof.
- Preservatives and antimicrobials such. P-hydroxybenzoic acid methyl, ethyl or propyl ester, sodium sorbate, sodium benzoate, bromochlorophene, phenylsalicylic acid ester, thymol and the like;
- anticalculus ingredients e.g. B. organophosphates such as 1-Hydroxyethan- 1 .1 - diphosphonic acid, 1-phosphonopropane-1, 2,3-tricarboxylic acid and others, the z. B. from US 3,488,419, DE 2224430 A1 and DE 2343196 A1 are known;
- sweeteners such as Sodium saccharin, sodium cyclamate, sucrose, lactose, maltose, fructose or Apartam®, (L-aspartyl-L-phenylalanine methyl ester), stivia extracts or their sweetening constituents, in particular ribeaudiosides;
- pigments such as For example, titanium dioxide
- Buffer substances such. Primary, secondary or tertiary alkali phosphates or citric acid / sodium citrate;
- a preferred embodiment of the cosmetic preparations are toothpastes in the form of an aqueous, pasty dispersion comprising polishing agents, humectants, viscosity regulators and, if appropriate, further customary components, and the mixture of menthofuran and menthol compounds in amounts of from 0.5 to 2% by weight. contain.
- a combination with aqueous-alcoholic solutions of various grades of essential oils, emulsifiers, astringent and toning drug extracts, anticalculus, antibacterial additives, and flavor remedies is readily possible.
- a further preferred embodiment of the invention is a mouthwash in the form of an aqueous or aqueous-alcoholic solution containing the mixture of menthofuran and menthol compounds in amounts of from 0.5 to 2% by weight.
- a mouthwash in the form of an aqueous or aqueous-alcoholic solution containing the mixture of menthofuran and menthol compounds in amounts of from 0.5 to 2% by weight.
- Hydrotropes such as, for example, ethanol, isopropyl alcohol, or polyols, can also be used to improve the flow behavior; These substances largely correspond to the initially described carriers.
- Polyols contemplated herein preferably have from 2 to 15 carbon atoms and at least two hydroxyl groups.
- the polyols may contain other functional groups, in particular amino groups, or be modified with nitrogen. Typical examples are
- Alkylene glycols such as ethylene glycol, diethylene glycol, propylene glycol, butylene glycol, hexylene glycol, and polyethylene glycols having an average molecular weight of 100 to 1, 000 daltons;
- MethyolENSen in particular trimethylolethane, trimethylolpropane, trimethylolbutane, pentaerythritol and dipentaerythritol;
- Lower alkyl glucosides especially those having 1 to 8 carbons in the alkyl radical, such as, for example, methyl and butyl glucoside;
- Sugar alcohols having 5 to 12 carbon atoms such as sorbitol or mannitol,
- sugars having 5 to 12 carbon atoms such as glucose or sucrose; • amino sugars, such as glucamine;
- Dialcoholamines such as diethanolamine or 2-amino-1,3-propanediol.
- Preservatives are, for example, phenoxyethanol, formaldehyde solution, parabens, pentanediol or sorbic acid and the known under the name Surfacine® silver complexes and listed in Appendix 6, Part A and B of the Cosmetics Regulation other classes.
- Dyes which may be used are those which are suitable and approved for cosmetic purposes, as compiled, for example, in the publication "Kosmetician Anlagenrbesch" of the Dye Commission of the Irish Kla Klastician, Verlag Chemie, Weinheim, 1984, pp. 81-106. Examples are Kochillerot A (Cl 16255), Patent Blue V (C.1.42051), Indigotin (C.1.73015), Chlorophyllin (C.1.75810), Quinoline Yellow (CI47005), Titanium Dioxide (C.1.77891), Indanthrene Blue RS (Cl 69800) and donut paint (CI58000). As a luminescent dye and luminol may be included. These dyes are usually used in concentrations of 0.001 to 0.1 wt .-%, based on the total mixture.
- the total amount of auxiliaries and additives may be 1 to 50, preferably 5 to 40 wt .-% - based on the means - amount.
- the preparation of the agent can be carried out by conventional cold or hot processes; It is preferable to work according to the phase inversion temperature method.
- the compounds of the formula (i), the formula (ii) and / or the formula (iii), or preferably ('E) -2-methyl-but-2-endicarboxylic acid diethyl ester, or the mixture of diethyl mesaconate, citraconic acid diethyl ester and Itaconsaurediethylester or the inventive fragrance mixtures containing detergents and cleaners (abbreviated as WSR agent) in the context of the present invention may be in solid form as powder, granules, tablets and the like, but also liquid, gel or pasty. It is preferably about Detergents suitable for both manual and machine washing, especially textiles. It can also be detergents or cleaning agents for industrial or household use.
- Cleaning agents can also be used, for example, for cleaning hard surfaces. These may be, for example, dishwashing detergents used for manual or automatic dishwashing. It can also be common industrial or household cleaners, which are used to clean hard surfaces such as furniture surfaces, tiles, tiles, wall and floor coverings. In addition to tableware, all other hard surfaces, in particular of glass, ceramic, plastic or metal, in household and in trade are also considered hard surfaces.
- the WSR agents may contain other commercially available ingredients such as surfactants, builders, bleaches, bleach activators, thickeners, enzymes, electrolytes, pH modifiers, dyes and perfumes, foam inhibitors, anti redeposition agents, optical brighteners,
- Grayness inhibitors anti-crease agents, antimicrobial agents, preservatives, antioxidants, antistatic agents, UV adsorbers,
- surfactants for the preparation of the detergents or cleaning agents it is also possible to use not only the nonionic surfactants but also anion, cation, ampho and / or nonionic surfactants and branched alkyl sulfates.
- nonionic surfactants are preferably alkoxylated, advantageously ethoxylated, especially primary alcohols having preferably 8 to 18 carbon atoms and an average of 1 to 12 moles of ethylene oxide (EO) per mole of alcohol used in which the alcohol radical linear or preferably in the 2-position may be methyl branched or contain linear and methyl-branched radicals in the mixture, as they are usually present in Oxoalkoholresten.
- EO ethylene oxide
- the preferred ethoxylated alcohols include, for example, C12-14-alcohols with 3 EO, 4 EO or 7 EO, C9-1 1 -alcohol with 7 EO, C13-5-alcohols with 3 EO, 5 EO, 7 EO or 8 EO, C12-18 alcohols with 3 EO, 5 EO or 7 EO and mixtures of these, such as mixtures of C12-4 alcohol with 3 EO and C12-8 alcohol with 7 EO.
- the degrees of ethoxylation given represent statistical means which, for a particular product, may be an integer or a fractional number.
- Preferred alcohol ethoxylates have a narrow homolog distribution (narrow rank ethoxylates, NRE).
- fatty alcohols with more than 12 EO can also be used. Examples include tallow fatty alcohol with 14 EO, 25 EO, 30 EO or 40 EO.
- Nonionic surfactants containing EO and PO groups together in the molecule can also be used according to the invention.
- block copolymers with EO-PO block units or PO-EO block units can be used, but also EO-PO-EO copolymers or PO-EO-PO copolymers.
- alkylpolyglycosides Another class of nonionic surfactants that can be used to advantage in the manufacture of detergents or cleaners are the alkylpolyglycosides (APG).
- APG alkylpolyglycosides
- Usable Alkypolyglycoside meet the general formula RO (G) Z, in which R is a linear or branched, in particular 2-methyl-branched, saturated or unsaturated, aliphatic radical having 8 to 22, preferably 12 to 18 carbon atoms and G is the Is a symbol which represents a glycose unit having 5 or 6 C atoms, preferably glucose.
- the glycosidation degree z is between 1, 0 and 4.0, preferably between 1, 0 and 2.0 and in particular between 1, 1 and 1, 4.
- Nonionic surfactants of the amine oxide type for example N-cocoalkyl-N, N-dimethylamine oxide and N-tallowalkyl-N, N-dihydroxyethylamine oxide, and the fatty acid alkanolamides may also be suitable for the preparation of the detergents or cleaners.
- the amount of these nonionic surfactants is preferably not more than that of the ethoxylated fatty alcohols, especially not more than half of them.
- Suitable surfactants are polyhydroxy fatty acid amides of the formula R-CO-N (R1) - [Z] in which RCO is an aliphatic acyl radical having 6 to 22 carbon atoms, R1 is hydrogen, an alkyl or hydroxyalkyl radical having 1 to 4 carbon atoms and [Z] represents a linear or branched polyhydroxyalkyl radical having 3 to 10 carbon atoms and 3 to 10 hydroxyl groups.
- the polyhydroxy fatty acid amides are known substances which can usually be obtained by reductive amination of a reducing sugar with ammonia, an alkylamine or an alkanolamine and subsequent acylation with a fatty acid, a fatty acid alkyl ester or a fatty acid chloride.
- the group of polyhydroxy fatty acid amides also includes compounds of the formula R-CO-N (R 1 -O-R 2) - [Z] in which R is a linear or branched alkyl or alkenyl radical having 7 to 12 carbon atoms, R 1 is a linear, branched one or a cyclic alkyl radical or an aryl radical having 2 to 8 carbon atoms and R 2 is a linear, branched or cyclic alkyl radical or an aryl radical or an oxyalkyl radical having 1 to 8 carbon atoms, preference being given to C 1-4 -alkyl or phenyl radicals and [Z ] is a linear polyhydroxyalkyl radical whose alkyl chain is substituted with at least two hydroxyl groups, or alkoxylated, preferably ethoxylated or propoxylated derivatives of this radical.
- [Z] is preferably obtained by reductive amination of a sugar, for example glucose, fructose, maltose, lactose, galactose, mannose or xylose.
- a sugar for example glucose, fructose, maltose, lactose, galactose, mannose or xylose.
- the N-alkoxy- or N-aryloxy-substituted compounds can then be converted into the desired polyhydroxy fatty acid amides by reaction with fatty acid methyl esters in the presence of an alkoxide as catalyst.
- the content of nonionic surfactants is the liquid detergents and cleaners preferably 5 to 30 wt .-%, preferably 7 to 20 wt.% And in particular 9 to 15 wt.%, Each based on the total agent.
- the anionic surfactants used are, for example, those of the sulfonate and sulfates type.
- surfactants of the sulfonate type are preferably C9-3-alkylbenzenesulfonates, olefinsulfonates, ie mixtures of alkene and hydroxyalkanesulfonates and disulfonates, as obtained for example from C12-8 monoolefins with terminal or internal double bond by sulfonating with gaseous sulfur trioxide and subsequent alkaline or acidic hydrolysis of the sulfonation, in consideration.
- alkanesulfonates which are obtained from C 12-8 alkanes, for example by sulfochlorination or sulfoxidation with subsequent hydrolysis or neutralization.
- esters of alpha-sulfo fatty acids for example the alpha-sulfonated methyl esters of hydrogenated coconut, palm kernel or tallow fatty acids.
- sulfonation products of unsaturated fatty acids for example oleic acid, in small amounts, preferably in amounts not above about 2 to 3 wt .-%.
- unsaturated fatty acids for example oleic acid
- alpha-sulfofatty acid alkyl esters which have an alkyl chain with not more than 4 C atoms in the ester group, for example methyl ester, ethyl ester, propyl ester and butyl ester.
- the methyl esters of the alpha sulfo fatty acids (MES), but also their saponified disalts are used.
- Suitable anionic surfactants are fatty acid derivatives of amino acids, for example N-methyltaurine (Tauride) and / or N-methylglycine (sarcosides). Particularly preferred are the sarcosides or the sarcosinates and here especially sarcosinates of higher and optionally monounsaturated or polyunsaturated fatty acids such as oleyl sarcosinate.
- Suitable anionic surfactants are sulfated fatty acid glycerol esters.
- Fatty acid glycerol esters are to be understood as meaning the mono-, di- and triesters and mixtures thereof, as obtained in the preparation by esterification of a monoglycerol with 1 to 3 moles of fatty acid or in the transesterification of triglycerides with 0.3 to 2 moles of glycerol.
- Preferred sulfated fatty acid glycerol esters are the sulfonation products of saturated fatty acids having 6 to 22 carbon atoms, for example caproic acid, caprylic acid, capric acid, myristic acid, lauric acid, palmitic acid, stearic acid or behenic acid.
- alk (en) ylsulfate are the alkali metal and in particular the sodium salts of sulfuric acid half esters of C12-C18 fatty alcohols, for example from coconut fatty alcohol, tallow fatty alcohol, lauryl, myristyl, cetyl or stearyl alcohol or the C10-C20 oxo alcohols and those half-esters of secondary alcohols of these chain lengths are preferred.
- alk (en) ylsulfates of said chain length which contain a synthetic, produced on a petrochemical basis straight-chain alkyl radical, which have an analogous degradation behavior as the adequate compounds based on oleochemical raw materials.
- C12-C16 alkyl sulfates and C12-C15 alkyl sulfates and C14-C15 alkyl sulfates are preferred.
- 2,3-Alkyl sulfates which can be obtained, for example, as commercial products of the Shell Oil Company under the name DAN (R), are suitable anionic surfactants.
- the sulfuric acid monoesters of straight-chain or branched C7-21 alcohols ethoxylated with from 1 to 6 moles of ethylene oxide such as 2-methyl-branched C9-1 1-alcohols having on average 3.5 moles of ethylene oxide (EO) or C12-18 Fatty alcohols containing 1 to 4 EO are suitable. Due to their high foaming behavior, they are only used in detergents in relatively small amounts, for example in amounts of from 1 to 5% by weight.
- Suitable anionic surfactants are also the salts of alkylsulfosuccinic acid, which are also referred to as sulfosuccinates or as sulfosuccinic acid esters and which are monoesters and / or diesters of sulfosuccinic acid with alcohols, preferably fatty alcohols and in particular ethoxylated fatty alcohols.
- alcohols preferably fatty alcohols and in particular ethoxylated fatty alcohols.
- Preferred sulfosuccinates contain C8-18 fatty alcohol residues or mixtures of these.
- Particularly preferred sulfosuccinates contain a fatty alcohol residue derived from ethoxylated fatty alcohols, which in themselves constitute nonionic surfactants (see description below).
- Sulfosuccinates whose fatty alcohol residues are derived from ethoxylated fatty alcohols with a narrow homolog distribution, are again particularly preferred.
- Alk (en) ylsuccinic acid with preferably 8 to 18 carbon atoms in the Al k (en) yl chain or salts thereof.
- Particularly preferred anionic surfactants are soaps. Suitable are saturated and unsaturated fatty acid soaps, such as the salts of lauric acid, myristic acid, palmitic acid, stearic acid, (hydrogenated) erucic acid and behenic acid and, in particular, soap mixtures derived from natural fatty acids, for example coconut, palm kernel, olive oil or tallow fatty acids.
- the anionic surfactants may be in the form of their sodium, potassium or ammonium salts and as soluble salts of organic bases, such as mono-, di- or triethanolamine.
- the anionic surfactants are preferably present in the form of their sodium or potassium salts, in particular in the form of the sodium salts.
- the content of preferred liquid detergents and cleaners to anionic surfactants is 1 to 30 wt.%, Preferably 4 to 25 wt.% And in particular 5 to 22 wt.%, Each based on the total agent. It is particularly preferred that the amount of fatty acid soap is at least 2% by weight and more preferably at least 3% by weight and especially preferably at least 4% by weight.
- gemini surfactants come into consideration for the preparation of detergents or cleaning agents according to the invention. These are generally understood as meaning those compounds which have two hydrophilic groups and two hydrophobic groups per molecule. These groups are usually separated by a so-called “spacer". This spacer is typically a carbon chain that should be long enough for the hydrophilic groups to be spaced sufficiently apart for them to act independently of each other.
- Such surfactants are generally characterized by an unusually low critical micelle concentration and the ability to greatly reduce the surface tension of the water. In exceptional cases, however, the term gemini surfactants is understood to mean not only dimeric but also trimeric surfactants.
- Gemini surfactants for the preparation of detergents or cleaners are, for example, sulfated hydroxy mixed ethers according to German patent application DE-A-43 21 022 or dimeralcohol bis- and trimer alcohol tris-sulfates and ether sulfates according to German patent application DE-A-195 03 061.
- End-capped dimeric and trimeric mixed ethers according to the German patent application DE-A-195 13 391 are distinguished in particular by their bi-and multifunctionality.
- the end-capped surfactants mentioned have good wetting properties and are low foaming, so that they are particularly suitable for use in machine washing or cleaning processes.
- the total surfactant content of the liquid washing and cleaning agent is preferably below 40% by weight and more preferably below 35% by weight, based on the total liquid detergent and cleaning agent.
- Suitable builders or builders which may be present in the liquid detergents and cleaners are, in particular, silicates, aluminum silicates (in particular zeolites), carbonates, organic cobuilders, phosphates, salts of organic di- and polycarboxylic acids and mixtures to name these substances.
- Suitable crystalline layered sodium silicates have the general formula NaMSixO2x + i * H2O, where M is sodium or hydrogen, x is a number from 1.9 to 4 and y is a number from 0 to 20 and preferred values for x 2, 3 or 4 are.
- Preferred crystalline layered silicates of the formula given are those in which M is sodium and x assumes the values 2 or 3.
- beta and delta sodium disilicates Na.sub.2Si.sub.2O.sub.s * yH.sub.2O are preferred.
- amorphous sodium silicates having a modulus Na 2 O: SiO 2 of from 1: 2 to 1: 3.3, preferably from 1: 2 to 1: 2.8 and in particular from 1: 2 to 1: 2.6, which Delayed and have secondary washing properties.
- the Dissolution delay compared to conventional amorphous sodium silicates may have been caused in various ways, for example by surface treatment, compounding, compaction / densification or by overdrying.
- the term "amorphous” is also understood to mean “X-ray amorphous”.
- the silicates do not yield sharp X-ray reflections typical of crystalline substances in X-ray diffraction experiments, but at most one or more maxima of the scattered X-rays which have a width of several degrees of diffraction angle. However, it may well even lead to particularly good builder properties if the silicate particles provide washed-out or even sharp diffraction maxima in electron diffraction experiments. This is to be interpreted as meaning that the products have microcrystalline regions of size 10 to a few hundred nm, with values of up to a maximum of 50 nm and in particular up to a maximum of 20 nm being preferred. Such so-called X-ray amorphous silicates also have a dissolution delay compared with the conventional water glasses. Especially preferred are compacted / compacted amorphous silicates, compounded amorphous silicates and overdried X-ray amorphous silicates.
- a usable fine crystalline, synthetic and bound water-containing zeolite is preferably zeolite A and / or P.
- zeolite P zeolite MAP TM (commercial product of Crosfield) is particularly preferred.
- zeolite X and mixtures of A, X and / or P are particularly preferred.
- Commercially available and preferably usable in the context of the present invention is, for example, a cocrystal of zeolite X and zeolite A (about 80% by weight of zeolite X) ), which is marketed under the brand name VEGOBOND AX (by the Sasol R) and by the formula: Na 2 O.
- the zeolite can be used as a spray-dried powder or else as undried, still moist, stabilized suspension of its preparation. In the event that the zeolite as a suspension is used, these may contain minor additions of nonionic surfactants as stabilizers, for example 1 to 3 wt.%, Based on zeolite, of ethoxylated Ci2-Ci8 fatty alcohols having 2 to 5 ethylene oxide groups, C12-C14 fatty alcohols having 4 to 5 ethylene oxide groups or ethoxylated isotridecanols. Suitable zeolites have an average particle size of less than 10 ⁇ m (volume distribution, measuring method: Coulter Counter) and preferably contain from 18 to 22% by weight, in particular from 20 to 22% by weight, of bound water.
- phosphates as builders are possible, unless such use should not be avoided for environmental reasons.
- Suitable builders are organic cobuilders, in particular polycarboxylates / polycarboxylic acids, polymeric polycarboxylates, aspartic acid, polyacetals, dextrins and also phosphonates.
- Polymeric polycarboxylates are, for example, the alkali metal salts of polyacrylic acid or polymethacrylic acid, for example those having a molecular weight of 500 to 70,000 g / mol.
- the molecular weights stated for polymeric polycarboxylates are weight-average molecular weights M w of the particular acid form, which were determined in principle by means of gel permeation chromatography (GPC), a UV detector being used. The measurement was carried out against an external polyacrylic acid standard, which provides realistic molecular weight values due to its structural relationship with the polymers investigated. These data differ significantly from the molecular weight data, in which polystyrene sulfonic acids are used as standard. The molar masses measured against polystyrenesulfonic acids are generally significantly higher than the molecular weights specified in this document.
- Suitable polymers are, in particular, polyacrylates which preferably have a molecular weight of 2,000 to 20,000 g / mol. Because of their superior solubility, this group can again be the short chain polyacrylates, the Molar masses of 2000 to 10,000 g / mol, and more preferably from 3000 to 5000 g / mol, be preferred.
- copolymeric polycarboxylates in particular those of acrylic acid with methacrylic acid and of acrylic acid or methacrylic acid with maleic acid.
- Copolymers of acrylic acid with maleic acid which contain 50 to 90% by weight of acrylic acid and 50 to 10% by weight of maleic acid have proven to be particularly suitable.
- Their relative molecular weight, based on free acids, is generally 2,000 to 70,000 g / mol, preferably 20,000 to 50,000 g / mol and in particular 30,000 to 40,000 g / mol.
- biodegradable polymers of more than two different monomer units for example those which contain as monomers salts of acrylic acid and maleic acid and vinyl alcohol or vinyl alcohol derivatives or as monomers salts of acrylic acid and 2-alkylallylsulfonic acid and sugar Derivatives.
- copolymers are those which preferably contain acrolein and acrylic acid / acrylic acid salts or acrolein and vinyl acetate as monomers.
- polymeric aminodicarboxylic acids are also suitable as further preferred builder substances.
- Particular preference is given to polyaspartic acids or their salts and derivatives which, in addition to co-builder properties, also have a bleach-stabilizing action.
- polyacetals which can be obtained by reacting dialdehydes with polyolcarboxylic acids which have 5 to 7 C atoms and at least 3 hydroxyl groups.
- Preferred polyacetals are obtained from dialdehydes such as glyoxal, glutaraldehyde, terephthalaldehyde and mixtures thereof and from polyol carboxylic acids such as gluconic acid and / or glucoheptonic acid.
- Further suitable organic builders are dextrins, for example, oligomers or polymers of carbohydrates, which can be replaced by partial Hydrolysis of starches can be obtained.
- the hydrolysis can be carried out by customary, for example acid or enzyme catalyzed processes.
- it is hydrolysis products having average molecular weights in the range of 400 to 500,000 g / mol.
- a polysaccharide with a dextrose equivalent (DE) in the range from 0.5 to 40, in particular from 2 to 30 is preferred, DE being a customary measure of the reducing action of a polysaccharide in comparison with dextrose, which has a DE of 100 ,
- DE dextrose equivalent
- Usable are both maltodextrins with a DE between 3 and 20 and dry glucose syrups with a DE between 20 and 37 and so-called yellow dextrins and white dextrins with higher molecular weights in the range of 2000 to 30,000 g / mol.
- the oxidized derivatives of such dextrins are their reaction products with oxidizing agents which are capable of oxidizing at least one alcohol function of the saccharide ring to the carboxylic acid function.
- a product oxidized at C6 of the saccharide ring may be particularly advantageous.
- a preferred dextrin is described in British Patent Application GB 9,419,091 B1.
- the oxidized derivatives of such dextrins are their reaction products with oxidizing agents which are capable of oxidizing at least one alcohol function of the saccharide ring to the carboxylic acid function.
- Such oxidized dextrins and processes for their preparation are known, for example, from European patent applications EP 0 322 202 A, EP 0427349 A, EP 0 472 042 A and EP 0542496 A and international patent applications WO 1992/018542 A, WO 1993/008251 A, WO 1994/028030 A, WO 1995/007303 A, WO 1995/012619 A and WO 1995/020608 A are known.
- a product oxidized on Ce of the saccharide ring may be particularly advantageous.
- Oxydisuccinates and other derivatives of disuccinates are also suitable co-builders.
- ethylenediamine ⁇ , ⁇ '-disuccinate (EDDS) is preferably used in the form of its sodium or magnesium salts.
- glycerol disuccinates and glycerol trisuccinates are also preferred.
- organic cobuilders are, for example, acetylated hydroxycarboxylic acids or salts thereof, which may optionally also be present in lactone form and which contain at least 4 carbon atoms and at least one hydroxyl group and a maximum of two acid groups.
- Such co-builders are described, for example, in international patent application WO 1995/020029 A.
- phosphonates are, in particular, hydroxyalkane and aminoalkane phosphonates.
- hydroxyalkane phosphonates 1-hydroxyethane-1,1-diphosphonate (HEDP) is of particular importance as a co-builder. It is preferably used as the sodium salt, the disodium salt neutral and the tetrasodium salt alkaline (pH 9).
- Ethylenediamine tetramethylene phosphonate (EDTMP) preferably comes as Aminoalkanphosphonate,
- Diethylenetriaminepentamethylenephosphonate and their higher homologues in question. They are preferably in the form of neutral sodium salts, eg. B. as the hexasodium salt of EDTMP or as hepta- and octa-sodium salt of DTPMP used.
- the builder used here is preferably HEDP from the class of phosphonates.
- the aminoalkanephosphonates also have a pronounced heavy metal binding capacity. Accordingly, in particular when the detergents and cleaning agents also contain bleach, it is preferable to use aminoalkanephosphonates, in particular DTPMP, or to use mixtures of the phosphonates mentioned for the preparation of the compositions.
- Further useful organic builders are also the polycarboxylic acids which can be used in the form of their sodium salts, polycarboxylic acids meaning those carboxylic acids which carry more than one acid function. These are, for example, citric acid, adipic acid, succinic acid, glutaric acid, malic acid, tartaric acid, maleic acid, fumaric acid, sugar acids, aminocarboxylic acids, nitrilotriacetic acid (NTA), if such use is not objectionable for ecological reasons, and mixtures of these.
- Preferred salts are the salts of polycarboxylic acids such as citric acid, adipic acid, succinic acid, glutaric acid, tartaric acid, sugar acids and mixtures thereof.
- the acids themselves can also be used.
- the acids typically also have the property of an acidifying component and thus also serve to set a lower and milder pH of detergents and / or cleaning agents.
- citric acid, succinic acid, glutaric acid, adipic acid, gluconic acid and any desired mixtures of these can be mentioned here.
- Bleaching agents and bleach catalysts Among the compounds used as bleaches in water H2O2, sodium perborate tetrahydrate and sodium perborate monohydrate are of particular importance. Other useful bleaching agents are, for example, sodium percarbonate, peroxypyrophosphates, citrate perhydrates and peroxyacids or peracids which yield H2O2, such as perbenzoates, peroxophthalates, diperazelaic acid, phthaloimino peracid or diperdodecanedioic acid. In order to achieve an improved bleaching effect when washing at temperatures of 60 ° C and below, bleach activators can be incorporated into the detergents and cleaners.
- bleach activators it is possible to use compounds which, under perhydrolysis conditions, give aliphatic peroxycarboxylic acids having preferably I to 10 C atoms, in particular 2 to 4 C atoms, and / or optionally substituted perbenzoic acid.
- Suitable substances are those which carry O- and / or N-acyl groups of the stated C atom number and / or optionally substituted benzoyl groups.
- polyacylated alkylenediamines in particular tetraacetylethylenediamine (TAED), acylated triazine derivatives, in particular 1,5-diacetyl-2,4-dioxohexahydro-1,3,5-triazine (DADHT), acylated glycolurils, in particular tetraacetylglycoluril (TAGU), N- Acylimides, in particular N-nonanoylsuccinimide (NOSI), acylated phenolsulfonates, in particular, nonanoyl or isononanoyloxybenzenesulfonate (n- or iso-NOBS), carboxylic anhydrides, in particular phthalic anhydride, acylated polyhydric alcohols, in particular triacetin, ethylene glycol diacetate and 2,5-diacetoxy-2,5-dihydrofuran.
- TAED tetraacetylethylene
- bleach catalysts can also be incorporated into the fabric treatment agents.
- These substances are bleach-enhancing transition metal salts or transition metal complexes such as Mn, Fe, Co, Ru or Mo saline complexes or carbonyl complexes.
- Mn, Fe, Co, Ru, Mo, Ti, V and Cu complexes with nitrogen-containing tripod ligands and Co, Fe, Cu and Ru ammine complexes can also be used as bleach catalysts.
- a liquid detergent and cleanser may contain a thickener.
- the thickener may include, for example, a polyacrylate thickener, xanthan gum, gellan gum, guar gum, alginate, carrageenan, carboxymethyl cellulose, bentonites, wellan gum, locust bean gum, agar-agar, tragacanth, gum arabic, pectins, polyoses, starch, dextrins, gelatin and casein include.
- modified natural substances such as modified starches and celluloses, examples which may be mentioned here include carboxymethylcellulose and other cellulose ethers, hydroxyethyl and -propylcellulose and core flour ethers, can be used as thickeners.
- the polyacrylic and polymethacrylic thickeners include, for example, the high molecular weight homopolymers of acrylic acid crosslinked with a polyalkenyl polyether, in particular an allyl ether of sucrose, pentaerythritol or propylene (INCI name according to the International Dictionary of Cosmetic Ingredients of The Cosmetic, Vol. Toiletry and Fragrance Association (CTFA) ": carbomer), also referred to as carboxyvinyl polymers.
- CTF Cosmetic, Vol. Toiletry and Fragrance Association
- Such polyacrylic acids are available, inter alia, from 3V Sigma under the trade name Polygel®, for example Polygel DA, and from BF Goodrich under the trade name Carbopol®, for example Carbopol 940 (molecular weight about 4,000,000), Carbopol 941 (molecular weight about 1,250,000) or Carbopol 934 (molecular weight about 3,000,000).
- acrylic acid copolymers (i) copolymers of two or more monomers selected from the group consisting of acrylic acid, methacrylic acid and their simple esters (INCI acrylates copolymer) preferably formed with C 1-4 alkanols, such as the copolymers of methacrylic acid, butyl acrylate and Methyl methacrylate (CAS designation according to Chemical Abstracts Service: 25035-69-2) or of butyl acrylate and methyl methacrylate (CAS 25852-37-3) and the example of the company Rohm and Haas under the trade names Aculyn® and Acusol® and of Degussa (Goldschmidt) under the trade name Tego® polymer, for example the anionic non-associating polymers Aculyn 22, Aculyn 28, Aculyn 33 (cross-linked), Acusol 810, Acusol 820, Acusol 823 and Acusol 830 (CAS 25852-37).
- acrylic acid copolymers preferably formed
- crosslinked high molecular weight acrylic acid copolymers such as those crosslinked with an allyl ether of sucrose or pentaerythritol copolymers of C10-30 alkyl acrylates with one or more monomers selected from the group consisting of acrylic acid, methacrylic acid and their simple, preferably with C 1-4 alkanols formed, esters (INCI Acrylates / Cl 0-30Alkyl Acrylate Crosspolymer) and which are available, for example, from the company.
- Carbopol® eg the hydrophobized Carbopol ETD 2623 and Carbopol 1382 (INCI Acrylat.es/C10-30Alkyl Acrylate Crosspolymer) and Carbopol Aqua 30 (formerly Carbopol EX 473).
- xanthan gum a microbial anionic heteropolysaccharide produced by xanthomonascampestris and some other species under aerobic conditions and having a molecular weight of 2 to 15 million daltons.
- Xanthan is formed from a chain of beta-1,4-linked glucose (cellulose) with side chains.
- the structure of the subgroups consists of glucose, mannose, glucuronic acid acetate and pyruvate, the number of pyruvate units determining the viscosity of the xanthan gum.
- a fatty alcohol is also suitable as thickener. Fatty alcohols may be branched or unbranched, of native or of petrochemical origin.
- Preferred fatty alcohols have a C chain length of 10 to 20 C atoms, preferably 12 to 18. Preference is given to using mixtures of different C chain lengths, such as tallow fatty alcohol or coconut oil fatty alcohol. Examples are Lorol® Spezial (C12-14-ROH) or Lorol® Technical (C12-18-ROH) (both ex Cognis).
- Preferred liquid detergents and cleaners contain 0.01 to 3% by weight, and preferably 0.1 to 1% by weight, of thickening agent, based on the total agent. The amount of thickener used depends on the type of thickener and the desired degree of thickening.
- Enzymes may contain enzymes in encapsulated form and / or directly in detergents and cleaners. Suitable enzymes are, in particular, those from the classes of the hydrolases such as the proteases, esterases, lipases or lipolytic enzymes, amylases, cellulases or other glycosyl hydrolases, hemicellulases, cutinases, beta-glucanases, oxidases, peroxidases, perhydrolases and / or laccases and mixtures the enzymes mentioned in question. All of these hydrolases in the wash contribute to the removal of stains such as proteinaceous, greasy or starchy stains and graying.
- hydrolases such as the proteases, esterases, lipases or lipolytic enzymes, amylases, cellulases or other glycosyl hydrolases, hemicellulases, cutinases, beta-glucanases, oxidases, peroxidases, perhydrolases and / or laccase
- cellulases and other glycosyl hydrolases contribute to color retention and to increasing the softness of the fabric by removing pilling and microfibrils.
- Oxireductases can also be used for bleaching or inhibiting color transfer.
- Particularly suitable are bacterial strains or fungi such as Bacillus subtilis, Bacillus borrow iformis, Streptomyceus griseus and Humicolainsolens derived enzymatic agents.
- subtilisin-type proteases and in particular proteases derived from Bacillus lentus are used.
- enzyme mixtures for example from protease and amylase or protease and lipase or lipolytic enzymes or protease and cellulase or from cellulase and lipase or lipolytic enzymes or from protease, amylase and lipase or lipolytic enzymes or protease, lipase or lipolytic enzymes and cellulase, but in particular protease and / or lipase-containing mixtures or mixtures with lipolytic enzymes of particular interest.
- lipolytic enzymes are the known cutinases. Peroxidases or oxidases have also proved suitable in some cases.
- Suitable amylases include, in particular, alpha-amylases, iso-amylases, pullulanases and pectinases.
- As cellulases are preferably cellobiohydrolases, endoglucanases and p-glucosidases, which also cellobiases be called, or mixtures thereof used. Since different cellulase types differ by their CMCase and avicelase activities, the desired activities can be set by targeted mixtures of the cellulases.
- the enzymes may be adsorbed to carriers to protect them from premature decomposition.
- the proportion of enzymes, of the enzyme liquid formulation (s) or of the enzyme granules directly in detergents and cleaners can be, for example, about 0.01 to 5% by weight, preferably 0.12 to about 2.5% by weight.
- washing and cleaning agent contains no enzymes.
- Electrolytes As electrolytes from the group of inorganic salts, a wide variety of different salts can be used. Preferred cations are the alkali and alkaline earth metals, preferred anions are the halides and sulfates. From a manufacturing point of view, the use of NaCl or MgC in the detergents and cleaners is preferred. The proportion of electrolytes in the washing and cleaning agent is usually 0.1 to 5 wt .-%.
- Non-aqueous solvents that can be used in the liquid detergents and cleaners, for example, from the group of monohydric or polyhydric alcohols, alkanolamines or glycol ethers, provided they are miscible with water in the specified concentration range.
- the solvents are selected from ethanol, n- or i-propanol, butanols, glycol, propane or butanediol, glycerol, diglycol, propyl or butyl diglycol, hexylene glycol, ethylene glycol methyl ether, ethylene glycol ethyl ether,
- Ethylene glycol propyl ether ethylene glycol mono-n-butyl ether, diethylene glycol methyl ether, diethylene glycol ethyl ether, propylene glycol methyl, ethyl or propyl ether, dipropylene glycol monomethyl or ethyl ether, diisopropylene glycol monomethyl or ethyl ether, methoxy, ethoxy or butoxy triglycol, 1-butoxyethoxy-2-one.
- Non-aqueous solvents may be used in the liquid detergents and cleaners in amounts of between 0.5 and 15% by weight, but preferably below 12% by weight and in particular below 9% by weight.
- Viscosity regulators The viscosity of the detergents and cleaners in liquid form can be measured by conventional standard methods (for example Brookfield LVT-II viscosimeter at 20 rpm and 20 ° C., spindle 3) and is preferably within the range for liquid detergents from 500 to 5000 mPas. Preferred liquid detergents and cleaners have viscosities of 700 to 4000 mPas, with values between 1000 and 3000 mPas being particularly preferred. The viscosity of fabric softeners is preferably 20 to 4000 mPas, with values between 40 and 2000 mPas being particularly preferred. The viscosity of fabric softeners is particularly preferably from 40 to 1000 mPas.
- pH adjuster In order to bring the pH of the liquid detergents and cleaners into the desired range, the use of pH adjusters may be indicated. Can be used here are all known acids or alkalis, unless their use is not for technical application or environmental reasons or for reasons of consumer protection prohibited. Usually, the amount of these adjusting agents does not exceed 7% by weight of the total formulation.
- the pH of liquid detergents and cleaners is preferably between 4 and 10, and preferably between 5.5 and 8.5.
- the pH of liquid fabric softeners is preferably between 1 and 6 and preferably between 1 .5 and 3.5.
- Dyes In order to improve the aesthetic impression of textile treatment agents, they can be dyed with suitable dyes. Preferred dyes, the selection of which presents no difficulty to the skilled person, have a high storage stability and insensitivity to the other ingredients of detergents and cleaning agents and to light and no pronounced substantivity to textile fibers so as not to stain them.
- Anti-redeposition agents are, for example, nonionic cellulose ethers such as methylcellulose and methylhydroxypropylcellulose with a methoxy group content of 15 to 30% by weight and hydroxypropyl groups of 1 to 15% by weight %, in each case based on the nonionic cellulose ether and the known from the prior art polymers of phthalic acid and / or terephthalic acid or derivatives thereof, in particular polymers of ethylene terephthalates and / or polyethylene and / or polypropylene glycol terephthalates or anionic and / or nonionic modified Derivatives of these Suitable derivatives include the sulfonated derivatives of the phthalic and terephthalic acid polymers.
- Optical brighteners can be added to laundry detergents and cleaners to eliminate graying and yellowing of the treated textile fabrics, which will be absorbed by the fiber and cause brightening and fake bleaching effects.
- the invisible ultraviolet radiation By converting the invisible ultraviolet radiation into visible wavelength light, the ultraviolet light absorbed from the sunlight is emitted as a faint bluish fluorescence and gives the whiteness of the grayed or yellowed wash pure white
- Suitable compounds are derived, for example, from the substance classes of 4,4'-diamino 2,2'-stilbenedisulfonic acids (flavonic acids), 4,4'-distyryl biphenyls,
- Methylumbelliferones coumarins, dihydroquinolinones, 1, 3-Diarylpyrazoline, Naphthalsaeureimide, benzoxazole, benzisoxazole and benzimidazole systems and substituted by heterocycles pyrene derivatives.
- the optical brighteners are usually used in amounts of from 0 to 0.3% by weight, based on the finished detergent and cleaner.
- Graying inhibitors have the task of keeping the dirt removed from the fiber suspended in the liquor and thus preventing the dirt from being rebuilt.
- water-soluble colloids are mostly of organic nature, for example glue, gelatin, salts of ether sulfonic acids or cellulose or salts of acidic sulfuric acid esters of cellulose or starch.
- water-soluble, acidic Group-containing polyamides are suitable for this purpose. It is also possible to use soluble starch preparations and starch products other than those mentioned above, for example degraded starch, aldehyde starches, etc. Polyvinylpyrrolidone is also useful.
- cellulose ethers such as carboxymethylcellulose (Na salt), methylcellulose, hydroxyalkylcellulose and mixed ethers such as methylhydroxyethylcellulose, methylhydroxypropylcellulose, methylcarboxymethylcellulose and mixtures thereof in amounts of from 0.1 to 5% by weight, based on the detergents and cleaners.
- Knitterschutzmittel Since textile fabrics, in particular from rayon, rayon, cotton and their mixtures, may tend to wrinkle, because the individual fibers are sensitive to bending, buckling, pressing and squeezing transverse to the fiber direction, the detergents and cleaning agents synthetic crease inhibitors contain. These include, for example, synthetic products based on fatty acids, fatty acid esters, fatty acid amides, alkylol esters, - alkylolamides or fatty alcohols, which are usually reacted with ethylene oxide, or products based on lecithin or modified phosphoric acid ester.
- Antimicrobial agents may contain antimicrobial agents to control microorganisms. Depending on the antimicrobial spectrum and mechanism of action, a distinction is made between bacteriostatic agents and bactericides, fungistatics and fungicides, etc. Important substances from these groups are, for example, benzalkonium chlorides, alkylarylsulfonates, halophenols and phenolmercuric acetate, and the compounds according to the invention can be completely dispensed with in these detergents and cleaners.
- the detergents and cleaners according to the invention may contain preservatives, it being preferred to use only those which have no or only a low skin-sensitizing potential.
- preservatives examples are sorbic acid and its salts, benzoic acid and its salts, salicylic acid and its salts, phenoxyethanol, 3-iodo-2-propynyl butylcarbamate, sodium N- (hydroxymethyl) glycinate, biphenyl-2-ol and Mixtures thereof.
- a suitable preservative is the solvent-free, aqueous combination of diazolidinyl urea, sodium benzoate and potassium sorbate (available as Euxyl® K 500ex Schülke and Mayr), which can be used in a pH range up to 7.
- preservatives based on organic acids and / or their salts are suitable for preserving the skin-friendly detergents and cleaners according to the invention.
- the detergents and cleaners may contain antioxidants.
- This class of compounds includes, for example, substituted phenols, hydroquinones, catechols and aromatic amines, as well as organic sulfides, polysulfides, dithiocarbamates, phosphites, phosphonates and vitamin E.
- Antistatic agents Increased wearing comfort may result from the additional use of antistatic agents, which are added to the detergents and cleaners. Antistatic agents increase the surface conductivity and thus allow an improved drainage of formed charges. Antistatic agents are generally substances with at least one hydrophilic molecule ligand and give a more or less hygroscopic film on the surfaces. These mostly surface-active antistatic agents can be subdivided into nitrogen-containing (amines, amides, quaternary ammonium compounds), phosphorus-containing (phosphoric acid esters) and sulfur-containing (alkyl sulfonates, alkyl sulfates) antistatic agents. Lauryl (or stearyl) dimethylbenzylammonium chlorides are suitable as antistatic agents for textile fabrics or as an additive to detergents and cleaners, wherein additionally a softening effect is achieved.
- silicone derivatives may be used in the fabric treatment agents. These additionally improve the rinsing out of the detergents and cleaning agents by their foam-inhibiting properties Properties.
- Preferred silicone derivatives are, for example, polydialkyl or alkylaryl siloxanes in which the alkyl groups have one to five carbon atoms and are completely or partially fluorinated.
- Preferred silicones are polydimethylsiloxanes, which may optionally be derivatized and are then amino-functional or quaternized or have Si-OH, Si-H and / or Si-Cl bonds.
- the viscosities of the preferred silicones are in the range between 100 and 100,000 mPas at 25 ° C, wherein the silicones in amounts between 0.2 and 5 wt .-%, based on the total detergent and cleaning agent can be used.
- UV absorbers Finally, the detergents and cleaners can also contain UV absorbers, which are absorbed by the treated textile fabrics and improve the light resistance of the fibers.
- Compounds exhibiting these desired properties include, for example, the non-radiative deactivation compounds and derivatives of benzophenone having substituents in the 2- and / or 4-position. Also suitable are substituted benzotriazoles, phenyl-substituted acrylates (cinnamic acid derivatives) in the 3-position, optionally with cyano groups in the 2-position, salicylates, organic Ni complexes and natural substances such as umbelliferone and the body's own urocanic acid.
- Heavy metal complexing agents In order to avoid the heavy metals catalyzed decomposition of certain detergent ingredients, substances that complex heavy metals can be used. Suitable heavy metal complexing agents are, for example, the alkali metal salts of ethylenediaminetetraacetic acid (EDTA) or nitrilotriacetic acid (NTA) and alkali metal salts of anionic polyelectrolytes such as polymaleates and polysulfonates.
- EDTA ethylenediaminetetraacetic acid
- NTA nitrilotriacetic acid
- anionic polyelectrolytes such as polymaleates and polysulfonates.
- a preferred class of complexing agents are the phosphonates which are contained in preferred textile treatment agents in amounts of from 0.01 to 2.5% by weight, preferably 0.02 to 2% by weight and in particular from 0.03 to 1 .5% by weight. These preferred compounds include in particular organophosphonates such as, for example, 1-hydroxyethane-1,1-di
- AMP Aminotri (methylenephosphonic acid)
- DTPMP diethylenetriamine penta (methylenephosphonic acid)
- DETPMP diethylenetriamine penta
- PBS-AM 2-phosphonobutane-1, 2,4- tricarboxylic acid
- the preparation of solid WSR agents can be carried out by the customary processes, such as, for example, tower spraying, fluidized-bed drying, agglomeration, powder mixing, tableting, granulation, especially SKET granulation.
- liquid WSR agents are also carried out by customary and known methods and processes, for example by simply mixing the ingredients in stirred tanks, water, non-aqueous solvents and surfactants are conveniently presented and the other ingredients are added in portions.
- liquid detergents and cleaners can be prepared by the acidic components such as the linear alkyl sulfonates, citric acid, boric acid, phosphonic acid, the fatty alcohol ether sulfates, etc. and the nonionic surfactants are presented.
- the solvent component is preferably also added at this time, but the addition may also be made at a later time.
- the thickening agent for example a polyacrylate.
- a base such as NaOH, KOH, triethanolamine or monoethanolamine followed by the fatty acid, if present, is added.
- the remaining ingredients and the remaining solvents of the aqueous liquid detergent and cleaner are added to the mixture and the pH is adjusted to about 8.5.
- the particles to be dispersed can be added and distributed homogeneously in the aqueous liquid washing and cleaning agent by mixing.
- the present invention relates to perfume oils or compositions perfumed or perfumed in this manner.
- the invention therefore relates to both perfume oils, cosmetic compositions, the application means, and the detergents and cleaners, including perfumed or perfumed products containing the compounds of the formula (i), of the formula (ii) and / or of the formula ( iii) in general, or the ('Ej-2-methyl-but-2-endicarboxylic acid diethyl ester per se, or, the Mesaconic acid diethyl ester in admixture with citraconic diethyl ester and diethyl itaconate in particular, or a corresponding fragrance mixture as described, these perfume oils or agents are selected from the group consisting of: perfume extracts, Eau de perfumes, Eau de Toilettes, shaving waters, Eau de Colognes , Pre-shave products, splash colognes and perfumed refreshing wipes and the perfuming of acidic, alkaline and neutral detergents, such as floor cleaners, window glass cleaners
- the invention according to a tenth aspect relates to agents selected from the group consisting of: solid and liquid soaps, shower gels, shampoos, shaving soaps, shaving creams, bath oils, cosmetic emulsions, skin creams and lotions, face creams and Facial lotions, sunscreen creams and lotions, after-sun creams and after-sun lotions, hand creams and lotions, foot creams and lotions, depilatory creams and lotions, aftershave creams and lotions, tanning lotions and lotions, Hair sprays, hair gels, hair lotions, hair conditioners, permanent and semipermanent hair dyes, hair styling hair lotions, hair creams and lotions, deodorants, underarm sprays, roll-ons, deodorants, deodorants and decorative cosmetics as well as perfume extras, eau de perfumes, eau de toilettes, Shaving waters, eau de colognes, pre-shave products, splash colognes, refreshing wipes, acidic, alkaline and
- An eleventh subject of the present invention relates to a process for the preparation of a mono- and / or diester of mesaconic acid comprising the following steps:
- an itaconic acid (preferably itaconic acid diethyl ester) is generally reacted with an approximately equimolar amount of acetic anhydride to form the cyclic anhydride and liberate acetic acid.
- the reaction usually takes place at temperatures in the range of 50 to 95 ° C, then the acetic acid is distilled off in vacuo.
- thermodynamically controlled isomerization of itaconic anhydride to citraconic anhydride occurs.
- the reaction is preferably carried out in a solvent and requires temperatures of 200 to 250 ° C. Again, the solvent is then removed.
- the final fourth step is the rearrangement of citraconic acid ester (preferably citraconic acid diethyl ester) into mesaconic acid (preferably the diethyl ester of mesaconic acid).
- This reaction preferably takes place in a suitable solvent such as MtBE at temperatures in the range of 170 to 200 ° C;
- a catalyst iodine is added to the mixture.
- the distillative removal of the solvent is again carried out.
- the process for the preparation of a mono- and / or diester of mesaconic acid is particularly preferred Step (ii) using a high-boiling solvent, preferably a polyalkylene glycol (PAG) having the structure: RO- [CH 2 -C (CH 3) HO] n - [CH 2 CH 2 O] m H.
- a high-boiling solvent preferably a polyalkylene glycol (PAG) having the structure: RO- [CH 2 -C (CH 3) HO] n - [CH 2 CH 2 O] m H.
- the high-boiling solvent preferably contains solvents having a boiling point greater than 250 ° C, more preferably greater than 300 ° C.
- PAG polyalkylene glycol
- Such are e.g. Synalox® 50-B SYNALOX TM 50-xB, known as lubricants, and alcohol-containing materials containing oxyethylene and oxypropylene groups with a single terminal hydroxyl group having the structure:
- a solvent system is used in step (ii) comprising a high-boiling solvent, preferably a polyalkylene glycol (PAG), having a boiling point greater than 150 ° C and further comprising a co-solvent having a boiling point of between 90 ° C and 120 ° C, preferably dioxane.
- a high-boiling solvent preferably a polyalkylene glycol (PAG)
- PAG polyalkylene glycol
- the yield could be increased, or remains high, when the protective solvent has a boiling point, so that it can also be distilled with the product in order to prevent the polymerization of the product in the distillation.
- the cosolvent or protective solvent has a boiling point of between 95 ° C and 1 10 ° C, more preferably from 100 ° C to 105 ° C. Suitable is dioxane.
- the co-solvent can be separated after the distillation step by common methods.
- Chlorinated aliphatic hydrocarbons such as, for example, 1,1,2-trichloroethane, pentachloroethane, 1-iodo-2-methylpropane, 1-chlorohexane, 1-chloro-2-ethylhexane; the chlorinated aromatic hydrocarbons and special chlorobenzenes, the chlorotoluenes,
- Ethers and more particularly the aliphatic ethers such as butyl ether, isobutyl ether, ethylhexyl ether, 1-butoxy-2-methoxyethane, 1,1-diethoxybutane, amyl ether, isoamyl ether, dipropoxymethane; the aromatic ethers, such as phenylpropyl ether, mesityl oxide,
- Nitrated compounds such as nitropropane, nitrobenzene,
- Aliphatic, cycloaliphatic or aromatic ketones preferably methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, methyl n-amyl ketone, methyl isoamyl ketone, cyclohexanone, methylcyclohexanone, diacetone alcohol.
- the co-solvents can also be used as a separate mixture.
- a thirteenth aspect of the present invention relates to a process for producing a mono- and / or diester of mesaconic acid, comprising the following steps:
- preparation process II be used as step (iv) in the preparation process I.
- the last rearrangement step is thus carried out according to the manufacturing process II, as it were following the steps (i) to (iii) in the manufacturing process I.
- the mono- and / or diester of mesaconic acid is an ('E) -2-methyl-but-2-endicarboxylic acid ester, preferably (E -2- Methyl-but-2-endicarboxylic acid diethyl ester.
- a preferred embodiment of the present invention therefore relates to a process for preparing ('E) -2-methyl-but-2-endicarboxylic acid diethyl ester comprising the following steps:
- the starting materials used are preferably mono- and / or diesters of citraconic acid with aliphatic, araliphatic or aromatic alcohols having 1 to 10 carbon atoms or diols having 2 to 6 hydroxyl groups.
- a fifteenth aspect of the invention relates to a method for imparting, modifying or enhancing a fruity, pear-like odor note in a fragrance mixture, a perfume oil, a cosmetic, a dressing or a detergent and cleaner, comprising the following steps:
- the compound (s) of the formula (i), of the formula (ii) and / or of the formula (iii) according to the invention are preferably in each case the (E -2-methyl-but-2-endicarboxylic acid diethyl ester (mesaconic acid diethyl ester) , Citraconic acid diethyl ester and Itaconsaurediethylester, or a mixture of (E -2-methyl-but-2-endicarboxylic acid diethyl ester with Citraconsaurediethylester and
- a sixteenth and seventeenth aspect of the invention relates to the use of compounds of the formula (i), of the formula (ii) and / or of the formula (iii) or mixtures thereof in general, or the ('Ej-2-methyl- But-2-endicarboxylic acid diethyl ester alone, or, Mesaconsaurediethylester in mixture with Citraconsaurediethylester and Itaconsaurediethylester in particular, or a corresponding fragrance mixture according to the invention on the one hand:
- Preferred compounds for this purpose are the compounds of the formula (i), of the formula (ii) and / or of the formula (iii) or mixtures thereof in general.
- step (ii) is carried out according to the rule below.
- EXAMPLE 6 Transparent deodorant sticks (formulation A, B) or deodorant cream sticks (formulation C, D)
- Part A Heat to about 85 ° C.
- chord with Mesaconsaurediethylester gives a natural intense pear-like impression.
- MSDEE Mesaconic acid diethyl ester
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Abstract
Description
Claims
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EP17771776.6A EP3559179A1 (de) | 2016-12-21 | 2017-09-27 | Riechstoffmischung |
BR112019012142-0A BR112019012142B1 (pt) | 2016-12-21 | 2017-09-27 | Mistura de fragrâncias |
CN202211167980.5A CN115322833A (zh) | 2016-12-21 | 2017-09-27 | 香料混合物 |
JP2019534329A JP6990707B2 (ja) | 2016-12-21 | 2017-09-27 | 香料混合物 |
US16/471,422 US10988434B2 (en) | 2016-12-21 | 2017-09-27 | Fragrance mixture |
CN201780079996.1A CN110099990B (zh) | 2016-12-21 | 2017-09-27 | 香料混合物 |
EP23185347.4A EP4282853A1 (de) | 2016-12-21 | 2017-09-27 | Verfahren zur herstellung von estern der mesaconsäure |
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CN115322833A (zh) | 2022-11-11 |
CN110099990A (zh) | 2019-08-06 |
BR112019012142B1 (pt) | 2023-10-17 |
EP3559179A1 (de) | 2019-10-30 |
JP6990707B2 (ja) | 2022-01-14 |
JP2020502354A (ja) | 2020-01-23 |
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US10988434B2 (en) | 2021-04-27 |
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US20200010402A1 (en) | 2020-01-09 |
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